NPASS Compound

Structure

CID327969 OpenBabel06191716192D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.2093 4.6098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8120 3.7183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0037 6.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5392 2.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0921 5.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7534 3.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3562 3.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6920 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 -1.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2300 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2298 0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6911 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 1.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1800 4.7116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3855 2.9285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5772 5.6031 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8460 -1.4653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6923 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3852 1.9525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5386 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6914 -0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5479 5.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5389 1.4642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5576 -1.4763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0193 1.9650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9452 6.5964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1214 4.9151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 3 19 1 0 0 0 0 7 34 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 26 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 19 28 1 0 0 0 0 20 4 1 1 0 0 0 20 23 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 21 27 2 0 0 0 0 22 30 1 6 0 0 0 23 29 1 6 0 0 0 24 30 1 6 0 0 0 25 31 2 0 0 0 0 26 27 1 0 0 0 0 26 32 2 0 0 0 0 27 29 1 0 0 0 0 28 33 2 0 0 0 0 28 34 1 0 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	515.189
LogP:	5.274
LogD:	5.176
LogS:	-5.358
# Rotatable Bonds:	6
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	5.03
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.0
MDCK Permeability:	1.6799855075078085e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	90.4443359375%
Volume Distribution (VD):	1.554
Pgp-substrate:	1.8143959045410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.219
CYP2D6-substrate:	0.558
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.806

ADMET: Excretion

Clearance (CL):	10.944
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.6
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.6
Skin Sensitization:	0.056
Carcinogencity:	0.051
Eye Corrosion:	0.011
Eye Irritation:	0.015
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC327969

Natural Product ID:	NPC327969
*Common Name:**	Methylantcinate A
IUPAC Name:	methyl (6R)-2-methyl-3-methylidene-6-[(4S,5S,10S,13R,14R,17R)-4,10,13-trimethyl-3,11-dioxo-2,4,5,6,7,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoate
Synonyms:
Standard InCHIKey:	JVQOVXPSHOWVQH-ZSGULCPNSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17(19(3)28(33)34-7)8-9-18(2)22-12-13-24-21-10-11-23-20(4)25(31)14-15-29(23,5)27(21)26(32)16-30(22,24)6/h18-20,22-24H,1,8-16H2,2-7H3/t18-,19?,20+,22-,23+,24+,29+,30-/m1/s1
SMILES:	COC(=O)C(C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CCC(=O)[C@H]2C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258116
PubChem CID:	52947057
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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
ED50	4
IC50	4
Others	16

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	2
Others	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	1500.0	nM	PMID[529458]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529458]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529458]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529458]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[529458]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37400.0	nM	PMID[529457]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24500.0	nM	PMID[529457]
NPT2	Others	Unspecified		Activity	=	23.63	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	59.73	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	27.71	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	62.33	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	13.2	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	15.35	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	14.3	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	9.09	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	66.86	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	87.07	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	59.19	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	69.06	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	56.5	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	57.8	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	41.07	%	PMID[529457]
NPT2	Others	Unspecified		Activity	=	52.55	%	PMID[529457]
NPT2	Others	Unspecified		IC50	=	16200.0	nM	PMID[529458]

☑ 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 NPC327969 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	175
0.1-0.2	1234
0.2-0.3	6595
0.3-0.4	15297
0.4-0.5	7170
0.5-0.6	6870
0.6-0.7	4126
0.7-0.8	1082
0.8-0.85	116
0.85-0.9	20
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321289
0.9744	High Similarity	NPC320801
0.9367	High Similarity	NPC168188
0.9367	High Similarity	NPC470015
0.9221	High Similarity	NPC469996
0.9136	High Similarity	NPC94531
0.9136	High Similarity	NPC123319
0.9136	High Similarity	NPC311702
0.9125	High Similarity	NPC271784
0.9125	High Similarity	NPC469561
0.8765	High Similarity	NPC320514
0.8765	High Similarity	NPC100297
0.8765	High Similarity	NPC260956
0.8765	High Similarity	NPC240302
0.8642	High Similarity	NPC201912
0.8642	High Similarity	NPC477372
0.8642	High Similarity	NPC38350
0.8636	High Similarity	NPC470016
0.8636	High Similarity	NPC317586
0.8608	High Similarity	NPC472300
0.8571	High Similarity	NPC195640
0.8554	High Similarity	NPC209882
0.8539	High Similarity	NPC328371
0.8523	High Similarity	NPC166906
0.8488	Intermediate Similarity	NPC305039
0.8471	Intermediate Similarity	NPC136948
0.8452	Intermediate Similarity	NPC473038
0.8452	Intermediate Similarity	NPC11711
0.8452	Intermediate Similarity	NPC29447
0.8452	Intermediate Similarity	NPC470223
0.8452	Intermediate Similarity	NPC323765
0.8434	Intermediate Similarity	NPC69279
0.8434	Intermediate Similarity	NPC83569
0.8427	Intermediate Similarity	NPC469995
0.8427	Intermediate Similarity	NPC174948
0.8427	Intermediate Similarity	NPC318282
0.8427	Intermediate Similarity	NPC173875
0.8415	Intermediate Similarity	NPC147066
0.8395	Intermediate Similarity	NPC477371
0.8391	Intermediate Similarity	NPC477147
0.8391	Intermediate Similarity	NPC477149
0.8372	Intermediate Similarity	NPC242864
0.8353	Intermediate Similarity	NPC475022
0.8353	Intermediate Similarity	NPC222613
0.8353	Intermediate Similarity	NPC118648
0.8353	Intermediate Similarity	NPC264127
0.8333	Intermediate Similarity	NPC305483
0.8333	Intermediate Similarity	NPC100391
0.8333	Intermediate Similarity	NPC328162
0.8333	Intermediate Similarity	NPC96859
0.8333	Intermediate Similarity	NPC473246
0.8333	Intermediate Similarity	NPC109512
0.8313	Intermediate Similarity	NPC133391
0.8295	Intermediate Similarity	NPC204341
0.8295	Intermediate Similarity	NPC218301
0.8295	Intermediate Similarity	NPC26888
0.8276	Intermediate Similarity	NPC473039
0.8276	Intermediate Similarity	NPC474889
0.8276	Intermediate Similarity	NPC54689
0.8276	Intermediate Similarity	NPC474570
0.8276	Intermediate Similarity	NPC214387
0.8276	Intermediate Similarity	NPC262043
0.8272	Intermediate Similarity	NPC63020
0.8256	Intermediate Similarity	NPC96496
0.825	Intermediate Similarity	NPC180886
0.825	Intermediate Similarity	NPC899
0.825	Intermediate Similarity	NPC474463
0.8242	Intermediate Similarity	NPC320306
0.8242	Intermediate Similarity	NPC43747
0.8235	Intermediate Similarity	NPC469948
0.8222	Intermediate Similarity	NPC171395
0.8214	Intermediate Similarity	NPC477373
0.8205	Intermediate Similarity	NPC223187
0.8202	Intermediate Similarity	NPC25750
0.8202	Intermediate Similarity	NPC206810
0.8193	Intermediate Similarity	NPC278459
0.8182	Intermediate Similarity	NPC148414
0.8182	Intermediate Similarity	NPC175628
0.8182	Intermediate Similarity	NPC111585
0.8172	Intermediate Similarity	NPC99411
0.8171	Intermediate Similarity	NPC472490
0.8171	Intermediate Similarity	NPC471475
0.8161	Intermediate Similarity	NPC471722
0.8161	Intermediate Similarity	NPC472220
0.8161	Intermediate Similarity	NPC28227
0.8161	Intermediate Similarity	NPC97884
0.8152	Intermediate Similarity	NPC197386
0.8152	Intermediate Similarity	NPC166745
0.8152	Intermediate Similarity	NPC235464
0.814	Intermediate Similarity	NPC145879
0.814	Intermediate Similarity	NPC28252
0.814	Intermediate Similarity	NPC155011
0.814	Intermediate Similarity	NPC474732
0.814	Intermediate Similarity	NPC474778
0.814	Intermediate Similarity	NPC72133
0.814	Intermediate Similarity	NPC474733
0.814	Intermediate Similarity	NPC31564
0.814	Intermediate Similarity	NPC220478
0.814	Intermediate Similarity	NPC55309
0.8132	Intermediate Similarity	NPC58052
0.8132	Intermediate Similarity	NPC125622
0.8132	Intermediate Similarity	NPC111684
0.8132	Intermediate Similarity	NPC472941
0.8132	Intermediate Similarity	NPC42042
0.8132	Intermediate Similarity	NPC456
0.8118	Intermediate Similarity	NPC164577
0.8118	Intermediate Similarity	NPC214043
0.8118	Intermediate Similarity	NPC85774
0.8111	Intermediate Similarity	NPC184870
0.8111	Intermediate Similarity	NPC56525
0.8101	Intermediate Similarity	NPC474228
0.8101	Intermediate Similarity	NPC303613
0.8101	Intermediate Similarity	NPC279241
0.8101	Intermediate Similarity	NPC470045
0.8101	Intermediate Similarity	NPC470044
0.8095	Intermediate Similarity	NPC142253
0.8095	Intermediate Similarity	NPC3511
0.8095	Intermediate Similarity	NPC296367
0.809	Intermediate Similarity	NPC297265
0.809	Intermediate Similarity	NPC154101
0.8085	Intermediate Similarity	NPC308726
0.8085	Intermediate Similarity	NPC119601
0.8077	Intermediate Similarity	NPC282593
0.8077	Intermediate Similarity	NPC159577
0.8077	Intermediate Similarity	NPC35734
0.8077	Intermediate Similarity	NPC307176
0.8072	Intermediate Similarity	NPC474956
0.8072	Intermediate Similarity	NPC267517
0.8068	Intermediate Similarity	NPC31985
0.8068	Intermediate Similarity	NPC177141
0.8068	Intermediate Similarity	NPC1015
0.8065	Intermediate Similarity	NPC316964
0.8065	Intermediate Similarity	NPC327431
0.8049	Intermediate Similarity	NPC4827
0.8049	Intermediate Similarity	NPC74410
0.8049	Intermediate Similarity	NPC321514
0.8046	Intermediate Similarity	NPC58063
0.8046	Intermediate Similarity	NPC159046
0.8046	Intermediate Similarity	NPC233836
0.8046	Intermediate Similarity	NPC187376
0.8046	Intermediate Similarity	NPC167877
0.8046	Intermediate Similarity	NPC128644
0.8046	Intermediate Similarity	NPC475740
0.8043	Intermediate Similarity	NPC108078
0.8043	Intermediate Similarity	NPC216904
0.8043	Intermediate Similarity	NPC18319
0.8043	Intermediate Similarity	NPC23680
0.8023	Intermediate Similarity	NPC2709
0.8023	Intermediate Similarity	NPC474680
0.8023	Intermediate Similarity	NPC470048
0.8023	Intermediate Similarity	NPC8571
0.8023	Intermediate Similarity	NPC189311
0.8022	Intermediate Similarity	NPC241156
0.8022	Intermediate Similarity	NPC33473
0.8022	Intermediate Similarity	NPC469599
0.8	Intermediate Similarity	NPC263780
0.8	Intermediate Similarity	NPC166797
0.8	Intermediate Similarity	NPC472226
0.8	Intermediate Similarity	NPC152897
0.8	Intermediate Similarity	NPC470046
0.8	Intermediate Similarity	NPC236390
0.8	Intermediate Similarity	NPC79117
0.8	Intermediate Similarity	NPC470047
0.8	Intermediate Similarity	NPC472225
0.8	Intermediate Similarity	NPC306928
0.8	Intermediate Similarity	NPC97913
0.8	Intermediate Similarity	NPC66429
0.8	Intermediate Similarity	NPC243866
0.7979	Intermediate Similarity	NPC302537
0.7979	Intermediate Similarity	NPC310981
0.7979	Intermediate Similarity	NPC473514
0.7979	Intermediate Similarity	NPC163372
0.7978	Intermediate Similarity	NPC474842
0.7978	Intermediate Similarity	NPC469400
0.7978	Intermediate Similarity	NPC471896
0.7978	Intermediate Similarity	NPC475965
0.7976	Intermediate Similarity	NPC471898
0.7976	Intermediate Similarity	NPC474085
0.7975	Intermediate Similarity	NPC115023
0.7957	Intermediate Similarity	NPC275439
0.7957	Intermediate Similarity	NPC176845
0.7957	Intermediate Similarity	NPC471717
0.7957	Intermediate Similarity	NPC112753
0.7955	Intermediate Similarity	NPC183546
0.7955	Intermediate Similarity	NPC472870
0.7955	Intermediate Similarity	NPC294480
0.7955	Intermediate Similarity	NPC131470
0.7955	Intermediate Similarity	NPC143767
0.7952	Intermediate Similarity	NPC274996
0.7952	Intermediate Similarity	NPC196827
0.7952	Intermediate Similarity	NPC90965
0.7952	Intermediate Similarity	NPC44083
0.7952	Intermediate Similarity	NPC118987
0.7952	Intermediate Similarity	NPC170793
0.7952	Intermediate Similarity	NPC153987
0.7949	Intermediate Similarity	NPC139397
0.7935	Intermediate Similarity	NPC3772
0.7935	Intermediate Similarity	NPC120708
0.7935	Intermediate Similarity	NPC7124
0.7935	Intermediate Similarity	NPC95565

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 NPC327969 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1560
0.2-0.3	4313
0.3-0.4	2145
0.4-0.5	519
0.5-0.6	202
0.6-0.7	162
0.7-0.8	74
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD5737	Approved
0.881	High Similarity	NPD6672	Approved
0.8571	High Similarity	NPD6409	Approved
0.8571	High Similarity	NPD7521	Approved
0.8571	High Similarity	NPD6684	Approved
0.8571	High Similarity	NPD5330	Approved
0.8571	High Similarity	NPD7334	Approved
0.8571	High Similarity	NPD7146	Approved
0.8506	High Similarity	NPD6050	Approved
0.8488	Intermediate Similarity	NPD6904	Approved
0.8488	Intermediate Similarity	NPD6080	Approved
0.8488	Intermediate Similarity	NPD6673	Approved
0.8391	Intermediate Similarity	NPD5692	Phase 3
0.8372	Intermediate Similarity	NPD6903	Approved
0.8372	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD5694	Approved
0.8228	Intermediate Similarity	NPD5733	Approved
0.8222	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD5695	Phase 3
0.8202	Intermediate Similarity	NPD6399	Phase 3
0.8182	Intermediate Similarity	NPD5207	Approved
0.8161	Intermediate Similarity	NPD5208	Approved
0.814	Intermediate Similarity	NPD6098	Approved
0.809	Intermediate Similarity	NPD5284	Approved
0.809	Intermediate Similarity	NPD5693	Phase 1
0.809	Intermediate Similarity	NPD5281	Approved
0.8077	Intermediate Similarity	NPD4747	Approved
0.8043	Intermediate Similarity	NPD6083	Phase 2
0.8043	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD4687	Approved
0.7975	Intermediate Similarity	NPD5276	Approved
0.7949	Intermediate Similarity	NPD4137	Phase 3
0.7907	Intermediate Similarity	NPD4786	Approved
0.7882	Intermediate Similarity	NPD4223	Phase 3
0.7882	Intermediate Similarity	NPD4221	Approved
0.7848	Intermediate Similarity	NPD4691	Approved
0.7826	Intermediate Similarity	NPD5654	Approved
0.7816	Intermediate Similarity	NPD5329	Approved
0.7766	Intermediate Similarity	NPD5696	Approved
0.7727	Intermediate Similarity	NPD5280	Approved
0.7727	Intermediate Similarity	NPD5690	Phase 2
0.7727	Intermediate Similarity	NPD5279	Phase 3
0.7727	Intermediate Similarity	NPD4694	Approved
0.7717	Intermediate Similarity	NPD6001	Approved
0.7701	Intermediate Similarity	NPD3668	Phase 3
0.7701	Intermediate Similarity	NPD3665	Phase 1
0.7701	Intermediate Similarity	NPD4197	Approved
0.7701	Intermediate Similarity	NPD3133	Approved
0.7701	Intermediate Similarity	NPD3666	Approved
0.7674	Intermediate Similarity	NPD3667	Approved
0.7667	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5328	Approved
0.7667	Intermediate Similarity	NPD4753	Phase 2
0.766	Intermediate Similarity	NPD5959	Approved
0.7619	Intermediate Similarity	NPD3617	Approved
0.7561	Intermediate Similarity	NPD4058	Approved
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.7528	Intermediate Similarity	NPD5205	Approved
0.7528	Intermediate Similarity	NPD4689	Approved
0.7528	Intermediate Similarity	NPD4690	Approved
0.7528	Intermediate Similarity	NPD4688	Approved
0.7528	Intermediate Similarity	NPD4693	Phase 3
0.7528	Intermediate Similarity	NPD4138	Approved
0.7527	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7900	Approved
0.7527	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6079	Approved
0.7475	Intermediate Similarity	NPD5739	Approved
0.7475	Intermediate Similarity	NPD6402	Approved
0.7475	Intermediate Similarity	NPD6675	Approved
0.7475	Intermediate Similarity	NPD7128	Approved
0.7475	Intermediate Similarity	NPD6008	Approved
0.7471	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6052	Approved
0.7444	Intermediate Similarity	NPD3573	Approved
0.7442	Intermediate Similarity	NPD4695	Discontinued
0.7375	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7732	Phase 3
0.7356	Intermediate Similarity	NPD4139	Approved
0.7356	Intermediate Similarity	NPD4692	Approved
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD6899	Approved
0.7327	Intermediate Similarity	NPD6881	Approved
0.7292	Intermediate Similarity	NPD7902	Approved
0.7263	Intermediate Similarity	NPD5210	Approved
0.7263	Intermediate Similarity	NPD4629	Approved
0.7255	Intermediate Similarity	NPD6372	Approved
0.7255	Intermediate Similarity	NPD6373	Approved
0.7234	Intermediate Similarity	NPD4202	Approved
0.7228	Intermediate Similarity	NPD6614	Approved
0.7228	Intermediate Similarity	NPD5701	Approved
0.7228	Intermediate Similarity	NPD5697	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4096	Approved
0.7191	Intermediate Similarity	NPD4788	Approved
0.7188	Intermediate Similarity	NPD4697	Phase 3
0.7188	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5221	Approved
0.7188	Intermediate Similarity	NPD5222	Approved
0.7184	Intermediate Similarity	NPD7290	Approved
0.7184	Intermediate Similarity	NPD6883	Approved
0.7184	Intermediate Similarity	NPD7102	Approved
0.7174	Intermediate Similarity	NPD4518	Approved
0.7157	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD6404	Discontinued
0.7128	Intermediate Similarity	NPD8035	Phase 2
0.7128	Intermediate Similarity	NPD8034	Phase 2
0.7126	Intermediate Similarity	NPD4195	Approved
0.7115	Intermediate Similarity	NPD6869	Approved
0.7115	Intermediate Similarity	NPD6847	Approved
0.7115	Intermediate Similarity	NPD8130	Phase 1
0.7115	Intermediate Similarity	NPD6650	Approved
0.7115	Intermediate Similarity	NPD6617	Approved
0.7115	Intermediate Similarity	NPD6649	Approved
0.7115	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5173	Approved
0.7113	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD6051	Approved
0.7087	Intermediate Similarity	NPD6014	Approved
0.7087	Intermediate Similarity	NPD6012	Approved
0.7087	Intermediate Similarity	NPD6013	Approved
0.7053	Intermediate Similarity	NPD5133	Approved
0.7048	Intermediate Similarity	NPD6882	Approved
0.7048	Intermediate Similarity	NPD8297	Approved
0.7041	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD1694	Approved
0.7011	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7614	Phase 1
0.7	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5286	Approved
0.697	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD5285	Approved
0.697	Remote Similarity	NPD4700	Approved
0.697	Remote Similarity	NPD7640	Approved
0.697	Remote Similarity	NPD4696	Approved
0.6957	Remote Similarity	NPD4519	Discontinued
0.6957	Remote Similarity	NPD4623	Approved
0.6947	Remote Similarity	NPD6411	Approved
0.6944	Remote Similarity	NPD7115	Discovery
0.6905	Remote Similarity	NPD6081	Approved
0.6905	Remote Similarity	NPD5777	Approved
0.69	Remote Similarity	NPD5223	Approved
0.6893	Remote Similarity	NPD6412	Phase 2
0.686	Remote Similarity	NPD7339	Approved
0.686	Remote Similarity	NPD6942	Approved
0.6852	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD5785	Approved
0.6832	Remote Similarity	NPD5226	Approved
0.6832	Remote Similarity	NPD4633	Approved
0.6832	Remote Similarity	NPD5211	Phase 2
0.6832	Remote Similarity	NPD5224	Approved
0.6832	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD4632	Approved
0.6813	Remote Similarity	NPD5362	Discontinued
0.6778	Remote Similarity	NPD5369	Approved
0.6765	Remote Similarity	NPD5174	Approved
0.6765	Remote Similarity	NPD4754	Approved
0.6765	Remote Similarity	NPD5175	Approved
0.6744	Remote Similarity	NPD4784	Approved
0.6744	Remote Similarity	NPD4785	Approved
0.6737	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6101	Approved
0.6727	Remote Similarity	NPD6335	Approved
0.6707	Remote Similarity	NPD4224	Phase 2
0.6706	Remote Similarity	NPD4243	Approved
0.6699	Remote Similarity	NPD5141	Approved
0.6697	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5363	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD5091	Approved
0.6636	Remote Similarity	NPD6317	Approved
0.6636	Remote Similarity	NPD6009	Approved
0.6635	Remote Similarity	NPD4768	Approved
0.6635	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD8028	Phase 2
0.6591	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6117	Approved
0.6577	Remote Similarity	NPD6314	Approved
0.6577	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6908	Approved
0.6549	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD4269	Approved
0.6522	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD4270	Approved
0.6517	Remote Similarity	NPD6116	Phase 1
0.6509	Remote Similarity	NPD5168	Approved
0.6509	Remote Similarity	NPD4729	Approved
0.6509	Remote Similarity	NPD4730	Approved
0.6509	Remote Similarity	NPD5128	Approved
0.6506	Remote Similarity	NPD7331	Phase 2
0.6505	Remote Similarity	NPD7632	Discontinued

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