NPASS Compound

Structure

CID90984 OpenBabel06191715432D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 -5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 -5.0949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5232 -6.5812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1705 -6.0460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 -6.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 -7.7402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 44 1 0 0 0 0 2 45 1 0 0 0 0 3 9 1 0 0 0 0 3 22 2 0 0 0 0 4 10 2 0 0 0 0 4 22 1 0 0 0 0 5 11 1 0 0 0 0 5 23 2 0 0 0 0 6 12 2 0 0 0 0 6 23 1 0 0 0 0 7 14 2 0 0 0 0 7 24 1 0 0 0 0 8 13 2 0 0 0 0 8 25 1 0 0 0 0 9 26 2 0 0 0 0 10 26 1 0 0 0 0 11 27 2 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 37 1 0 0 0 0 18 38 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 20 31 2 0 0 0 0 21 25 2 0 0 0 0 21 30 1 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 33 1 0 0 0 0 28 35 2 0 0 0 0 29 30 2 0 0 0 0 29 41 1 0 0 0 0 30 44 1 0 0 0 0 31 35 1 0 0 0 0 31 45 1 0 0 0 0 32 37 2 3 0 0 0 32 42 1 0 0 0 0 33 34 1 0 0 0 0 33 36 1 1 0 0 0 34 25 1 6 0 0 0 34 46 1 0 0 0 0 35 46 1 0 0 0 0 36 38 2 3 0 0 0 36 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.25
Volume:	641.198
LogP:	3.926
LogD:	3.615
LogS:	-4.521
# Rotatable Bonds:	14
TPSA:	146.58
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	3.595
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.51
MDCK Permeability:	5.8928148973791394e-06
Pgp-inhibitor:	0.719
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.255
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.62610626220703%
Volume Distribution (VD):	0.528
Pgp-substrate:	1.0096806287765503%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.71
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	5.508
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.678
Human Hepatotoxicity (H-HT):	0.643
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.689
Rat Oral Acute Toxicity:	0.297
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.906
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.035

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC90984

Natural Product ID:	NPC90984
*Common Name:**	Grossamide
IUPAC Name:	(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(E)-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
Synonyms:	Grossamide
Standard InCHIKey:	DROXVBRNXCRUHP-YRKLVFRVSA-N
Standard InCHI:	InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+/t33-,34+/m1/s1
SMILES:	COc1cc(/C=C/C(=NCCc2ccc(cc2)O)O)cc2c1O[C@H]([C@@H]2C(=NCCc1ccc(cc1)O)O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500729
PubChem CID:	6440658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO7451	Hibiscus cannabinus	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21512441]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7451	Hibiscus cannabinus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7451	Hibiscus cannabinus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7451	Hibiscus cannabinus	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	3
IC50	3
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	33000.0	nM	PMID[536874]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	39300.0	nM	PMID[536876]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	24700.0	nM	PMID[536876]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	21000.0	nM	PMID[536875]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	24000.0	nM	PMID[536875]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	100000.0	nM	PMID[536875]
NPT35	Others	n.a.		K	=	2.32	n.a.	PMID[536875]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC90984 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	1286
0.2-0.3	4525
0.3-0.4	12420
0.4-0.5	5483
0.5-0.6	7475
0.6-0.7	8619
0.7-0.8	2449
0.8-0.85	157
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8938	High Similarity	NPC179250
0.8938	High Similarity	NPC50380
0.8839	High Similarity	NPC471032
0.8839	High Similarity	NPC470935
0.8742	High Similarity	NPC107602
0.8693	High Similarity	NPC222039
0.8693	High Similarity	NPC100478
0.8645	High Similarity	NPC5462
0.8616	High Similarity	NPC275027
0.8571	High Similarity	NPC470372
0.8553	High Similarity	NPC127402
0.8509	High Similarity	NPC115203
0.8442	Intermediate Similarity	NPC260842
0.8438	Intermediate Similarity	NPC477612
0.8418	Intermediate Similarity	NPC277857
0.8418	Intermediate Similarity	NPC260397
0.8418	Intermediate Similarity	NPC115144
0.8385	Intermediate Similarity	NPC324517
0.8385	Intermediate Similarity	NPC321972
0.8385	Intermediate Similarity	NPC329343
0.8354	Intermediate Similarity	NPC181615
0.8344	Intermediate Similarity	NPC157333
0.8313	Intermediate Similarity	NPC227516
0.8313	Intermediate Similarity	NPC20757
0.8312	Intermediate Similarity	NPC77861
0.8312	Intermediate Similarity	NPC156502
0.8312	Intermediate Similarity	NPC263367
0.8312	Intermediate Similarity	NPC10737
0.8312	Intermediate Similarity	NPC209985
0.8312	Intermediate Similarity	NPC477939
0.8312	Intermediate Similarity	NPC29799
0.8312	Intermediate Similarity	NPC54743
0.8312	Intermediate Similarity	NPC177160
0.8303	Intermediate Similarity	NPC470827
0.8303	Intermediate Similarity	NPC125495
0.8301	Intermediate Similarity	NPC193026
0.8301	Intermediate Similarity	NPC49603
0.8301	Intermediate Similarity	NPC187616
0.8263	Intermediate Similarity	NPC470936
0.8261	Intermediate Similarity	NPC470826
0.8261	Intermediate Similarity	NPC473266
0.8261	Intermediate Similarity	NPC470098
0.8261	Intermediate Similarity	NPC211561
0.8258	Intermediate Similarity	NPC299583
0.8253	Intermediate Similarity	NPC470828
0.825	Intermediate Similarity	NPC327412
0.825	Intermediate Similarity	NPC320970
0.825	Intermediate Similarity	NPC328567
0.825	Intermediate Similarity	NPC320671
0.8247	Intermediate Similarity	NPC93783
0.8199	Intermediate Similarity	NPC226153
0.8199	Intermediate Similarity	NPC304048
0.8194	Intermediate Similarity	NPC204848
0.8194	Intermediate Similarity	NPC41473
0.8194	Intermediate Similarity	NPC160607
0.8194	Intermediate Similarity	NPC14600
0.8194	Intermediate Similarity	NPC312770
0.8187	Intermediate Similarity	NPC317053
0.8187	Intermediate Similarity	NPC324492
0.8182	Intermediate Similarity	NPC202104
0.8176	Intermediate Similarity	NPC304894
0.8176	Intermediate Similarity	NPC15659
0.8165	Intermediate Similarity	NPC131971
0.8153	Intermediate Similarity	NPC22317
0.8153	Intermediate Similarity	NPC55793
0.8137	Intermediate Similarity	NPC202742
0.8137	Intermediate Similarity	NPC99183
0.8137	Intermediate Similarity	NPC18185
0.8137	Intermediate Similarity	NPC114505
0.8137	Intermediate Similarity	NPC58190
0.8137	Intermediate Similarity	NPC263940
0.8137	Intermediate Similarity	NPC262911
0.8137	Intermediate Similarity	NPC213074
0.8137	Intermediate Similarity	NPC294558
0.8137	Intermediate Similarity	NPC82917
0.8137	Intermediate Similarity	NPC108811
0.8137	Intermediate Similarity	NPC31325
0.8137	Intermediate Similarity	NPC204770
0.8137	Intermediate Similarity	NPC224674
0.8137	Intermediate Similarity	NPC170103
0.8137	Intermediate Similarity	NPC70409
0.8137	Intermediate Similarity	NPC193473
0.8137	Intermediate Similarity	NPC236202
0.8137	Intermediate Similarity	NPC15956
0.8137	Intermediate Similarity	NPC275284
0.8117	Intermediate Similarity	NPC26394
0.8113	Intermediate Similarity	NPC173203
0.8113	Intermediate Similarity	NPC163508
0.811	Intermediate Similarity	NPC279406
0.811	Intermediate Similarity	NPC226809
0.8101	Intermediate Similarity	NPC471414
0.8101	Intermediate Similarity	NPC87725
0.8101	Intermediate Similarity	NPC263261
0.8086	Intermediate Similarity	NPC329836
0.8086	Intermediate Similarity	NPC281549
0.8075	Intermediate Similarity	NPC93610
0.8075	Intermediate Similarity	NPC241846
0.8075	Intermediate Similarity	NPC96576
0.8063	Intermediate Similarity	NPC471415
0.8063	Intermediate Similarity	NPC470097
0.8063	Intermediate Similarity	NPC185388
0.8063	Intermediate Similarity	NPC63879
0.8063	Intermediate Similarity	NPC45257
0.8063	Intermediate Similarity	NPC114119
0.8063	Intermediate Similarity	NPC93323
0.8063	Intermediate Similarity	NPC238216
0.8063	Intermediate Similarity	NPC84684
0.8063	Intermediate Similarity	NPC280092
0.8063	Intermediate Similarity	NPC12641
0.8063	Intermediate Similarity	NPC208994
0.8061	Intermediate Similarity	NPC470769
0.8061	Intermediate Similarity	NPC224161
0.8052	Intermediate Similarity	NPC230219
0.805	Intermediate Similarity	NPC253878
0.8047	Intermediate Similarity	NPC216916
0.8045	Intermediate Similarity	NPC41122
0.8045	Intermediate Similarity	NPC318805
0.8039	Intermediate Similarity	NPC114102
0.8038	Intermediate Similarity	NPC184797
0.8038	Intermediate Similarity	NPC309124
0.8038	Intermediate Similarity	NPC291101
0.8038	Intermediate Similarity	NPC266197
0.8037	Intermediate Similarity	NPC318373
0.8037	Intermediate Similarity	NPC321657
0.8037	Intermediate Similarity	NPC476969
0.8036	Intermediate Similarity	NPC478269
0.8025	Intermediate Similarity	NPC16269
0.8025	Intermediate Similarity	NPC21776
0.8025	Intermediate Similarity	NPC296898
0.8012	Intermediate Similarity	NPC43508
0.8012	Intermediate Similarity	NPC476301
0.8012	Intermediate Similarity	NPC46335
0.8	Intermediate Similarity	NPC102044
0.8	Intermediate Similarity	NPC47633
0.8	Intermediate Similarity	NPC85264
0.7988	Intermediate Similarity	NPC52475
0.7988	Intermediate Similarity	NPC98624
0.7987	Intermediate Similarity	NPC178054
0.7987	Intermediate Similarity	NPC214869
0.7975	Intermediate Similarity	NPC260741
0.7975	Intermediate Similarity	NPC473739
0.7975	Intermediate Similarity	NPC232164
0.7975	Intermediate Similarity	NPC236306
0.7975	Intermediate Similarity	NPC70682
0.7974	Intermediate Similarity	NPC52029
0.7974	Intermediate Similarity	NPC195749
0.7974	Intermediate Similarity	NPC35961
0.7967	Intermediate Similarity	NPC234318
0.7953	Intermediate Similarity	NPC45943
0.795	Intermediate Similarity	NPC284881
0.795	Intermediate Similarity	NPC473108
0.795	Intermediate Similarity	NPC474444
0.795	Intermediate Similarity	NPC79429
0.795	Intermediate Similarity	NPC28440
0.795	Intermediate Similarity	NPC217635
0.795	Intermediate Similarity	NPC93433
0.795	Intermediate Similarity	NPC264706
0.795	Intermediate Similarity	NPC471667
0.795	Intermediate Similarity	NPC171932
0.795	Intermediate Similarity	NPC313414
0.7949	Intermediate Similarity	NPC471942
0.7949	Intermediate Similarity	NPC478085
0.7941	Intermediate Similarity	NPC478267
0.7939	Intermediate Similarity	NPC18614
0.7937	Intermediate Similarity	NPC59841
0.7937	Intermediate Similarity	NPC204347
0.7937	Intermediate Similarity	NPC2613
0.7937	Intermediate Similarity	NPC476356
0.7937	Intermediate Similarity	NPC107161
0.7937	Intermediate Similarity	NPC475891
0.7935	Intermediate Similarity	NPC18842
0.7925	Intermediate Similarity	NPC254759
0.7925	Intermediate Similarity	NPC472091
0.7925	Intermediate Similarity	NPC262189
0.7925	Intermediate Similarity	NPC472092
0.7925	Intermediate Similarity	NPC160283
0.7925	Intermediate Similarity	NPC472090
0.7922	Intermediate Similarity	NPC64201
0.7922	Intermediate Similarity	NPC92164
0.7922	Intermediate Similarity	NPC241522
0.7922	Intermediate Similarity	NPC42300
0.7922	Intermediate Similarity	NPC242807
0.7922	Intermediate Similarity	NPC77040
0.7922	Intermediate Similarity	NPC174495
0.7922	Intermediate Similarity	NPC187998
0.7922	Intermediate Similarity	NPC153739
0.7922	Intermediate Similarity	NPC145305
0.7922	Intermediate Similarity	NPC257582
0.7914	Intermediate Similarity	NPC101376
0.7914	Intermediate Similarity	NPC262297
0.7911	Intermediate Similarity	NPC477938
0.7911	Intermediate Similarity	NPC474390
0.7908	Intermediate Similarity	NPC128208
0.7908	Intermediate Similarity	NPC45774
0.7908	Intermediate Similarity	NPC21867
0.7908	Intermediate Similarity	NPC155838
0.7908	Intermediate Similarity	NPC282703
0.7908	Intermediate Similarity	NPC11258
0.7908	Intermediate Similarity	NPC184733
0.7908	Intermediate Similarity	NPC129570

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC90984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	686
0.2-0.3	1066
0.3-0.4	2496
0.4-0.5	2297
0.5-0.6	1478
0.6-0.7	805
0.7-0.8	148
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD6331	Phase 2
0.7976	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD4123	Phase 3
0.7826	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2161	Phase 2
0.7798	Intermediate Similarity	NPD5772	Approved
0.7798	Intermediate Similarity	NPD5773	Approved
0.7778	Intermediate Similarity	NPD7906	Approved
0.7725	Intermediate Similarity	NPD4678	Approved
0.7725	Intermediate Similarity	NPD4675	Approved
0.7709	Intermediate Similarity	NPD8054	Approved
0.7709	Intermediate Similarity	NPD8053	Approved
0.7697	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD52	Approved
0.7697	Intermediate Similarity	NPD7526	Approved
0.7679	Intermediate Similarity	NPD6072	Discontinued
0.7654	Intermediate Similarity	NPD7311	Approved
0.7654	Intermediate Similarity	NPD7310	Approved
0.7654	Intermediate Similarity	NPD7312	Approved
0.7654	Intermediate Similarity	NPD7313	Approved
0.7633	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7309	Approved
0.761	Intermediate Similarity	NPD2157	Approved
0.7602	Intermediate Similarity	NPD7773	Phase 2
0.76	Intermediate Similarity	NPD2489	Approved
0.76	Intermediate Similarity	NPD27	Approved
0.7595	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3051	Approved
0.7558	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7833	Phase 2
0.7558	Intermediate Similarity	NPD7831	Phase 2
0.7556	Intermediate Similarity	NPD4577	Approved
0.7556	Intermediate Similarity	NPD4578	Approved
0.7545	Intermediate Similarity	NPD2122	Discontinued
0.7543	Intermediate Similarity	NPD2970	Approved
0.7543	Intermediate Similarity	NPD2969	Approved
0.7532	Intermediate Similarity	NPD2674	Phase 3
0.7532	Intermediate Similarity	NPD7477	Discontinued
0.7531	Intermediate Similarity	NPD1375	Discontinued
0.753	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4663	Approved
0.7486	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD3144	Approved
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3145	Approved
0.7457	Intermediate Similarity	NPD8070	Approved
0.7456	Intermediate Similarity	NPD4005	Discontinued
0.7427	Intermediate Similarity	NPD5722	Discontinued
0.7425	Intermediate Similarity	NPD7020	Approved
0.7425	Intermediate Similarity	NPD7019	Approved
0.7423	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3027	Phase 3
0.7389	Intermediate Similarity	NPD1712	Approved
0.7386	Intermediate Similarity	NPD6071	Discontinued
0.7384	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7037	Approved
0.7378	Intermediate Similarity	NPD7153	Discontinued
0.7375	Intermediate Similarity	NPD1558	Phase 1
0.7374	Intermediate Similarity	NPD8156	Discontinued
0.7342	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7341	Intermediate Similarity	NPD2563	Approved
0.7341	Intermediate Similarity	NPD2560	Approved
0.7333	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7321	Intermediate Similarity	NPD7447	Phase 1
0.7321	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8252	Approved
0.7318	Intermediate Similarity	NPD8099	Discontinued
0.7318	Intermediate Similarity	NPD8251	Approved
0.7278	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7213	Phase 3
0.7262	Intermediate Similarity	NPD7212	Phase 2
0.7244	Intermediate Similarity	NPD1669	Approved
0.7233	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4237	Approved
0.7229	Intermediate Similarity	NPD4236	Phase 3
0.7229	Intermediate Similarity	NPD3060	Approved
0.7219	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6584	Phase 3
0.7213	Intermediate Similarity	NPD7549	Discontinued
0.7209	Intermediate Similarity	NPD6502	Phase 2
0.7197	Intermediate Similarity	NPD2922	Phase 1
0.7195	Intermediate Similarity	NPD4108	Discontinued
0.7186	Intermediate Similarity	NPD7466	Approved
0.7184	Intermediate Similarity	NPD5929	Approved
0.7184	Intermediate Similarity	NPD2977	Approved
0.7184	Intermediate Similarity	NPD2978	Approved
0.7159	Intermediate Similarity	NPD4055	Discovery
0.7159	Intermediate Similarity	NPD5604	Discontinued
0.7151	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5976	Discontinued
0.7128	Intermediate Similarity	NPD2488	Approved
0.7128	Intermediate Similarity	NPD2490	Approved
0.7126	Intermediate Similarity	NPD4162	Approved
0.7119	Intermediate Similarity	NPD6234	Discontinued
0.7113	Intermediate Similarity	NPD7590	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4481	Phase 3
0.7104	Intermediate Similarity	NPD7007	Discovery
0.7101	Intermediate Similarity	NPD7124	Phase 2
0.7101	Intermediate Similarity	NPD6667	Approved
0.7101	Intermediate Similarity	NPD6666	Approved
0.7099	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4666	Phase 3
0.7079	Intermediate Similarity	NPD6746	Phase 2
0.7073	Intermediate Similarity	NPD4097	Suspended
0.7066	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2493	Approved
0.7062	Intermediate Similarity	NPD2494	Approved
0.7055	Intermediate Similarity	NPD2238	Phase 2
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD4583	Approved
0.7041	Intermediate Similarity	NPD2677	Approved
0.7041	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5241	Discontinued
0.7041	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4582	Approved
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD5109	Approved
0.7037	Intermediate Similarity	NPD5110	Phase 2
0.7037	Intermediate Similarity	NPD5111	Phase 2
0.7033	Intermediate Similarity	NPD7228	Approved
0.703	Intermediate Similarity	NPD6896	Approved
0.703	Intermediate Similarity	NPD6895	Approved
0.7025	Intermediate Similarity	NPD6582	Phase 2
0.7025	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6583	Phase 3
0.7024	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5709	Phase 3
0.7017	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4873	Discontinued
0.6995	Remote Similarity	NPD6042	Phase 2
0.6995	Remote Similarity	NPD42	Phase 2
0.6994	Remote Similarity	NPD840	Approved
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6994	Remote Similarity	NPD839	Approved
0.6994	Remote Similarity	NPD4210	Discontinued
0.699	Remote Similarity	NPD4002	Approved
0.699	Remote Similarity	NPD4004	Approved
0.6989	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8651	Approved
0.6977	Remote Similarity	NPD6090	Discontinued
0.6974	Remote Similarity	NPD3450	Approved
0.6974	Remote Similarity	NPD3452	Approved
0.6971	Remote Similarity	NPD7438	Suspended
0.6971	Remote Similarity	NPD3778	Approved
0.6959	Remote Similarity	NPD4357	Discontinued
0.6959	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7047	Phase 3
0.6944	Remote Similarity	NPD7199	Phase 2
0.6941	Remote Similarity	NPD2219	Phase 1
0.6941	Remote Similarity	NPD3692	Discontinued
0.6935	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5718	Phase 2
0.6932	Remote Similarity	NPD37	Approved
0.6932	Remote Similarity	NPD1934	Approved
0.6931	Remote Similarity	NPD6842	Approved
0.6931	Remote Similarity	NPD6841	Approved
0.6931	Remote Similarity	NPD6843	Phase 3
0.6919	Remote Similarity	NPD3985	Discontinued
0.6919	Remote Similarity	NPD4739	Approved
0.6915	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4967	Phase 2
0.691	Remote Similarity	NPD4965	Approved
0.691	Remote Similarity	NPD4966	Approved
0.6905	Remote Similarity	NPD7030	Discontinued
0.6899	Remote Similarity	NPD1610	Phase 2
0.6895	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3489	Phase 3
0.6881	Remote Similarity	NPD7827	Phase 1
0.6875	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5314	Approved
0.6863	Remote Similarity	NPD5283	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data