NPASS Compound

Structure

NPC190663 OpenBabel07101718332D 41 42 0 0 1 0 0 0 0 0999 V2000 1.4468 -2.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1771 -3.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3345 3.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5853 5.8714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2517 1.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0827 6.2018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9491 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 -0.7874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2770 4.6484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5517 -3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9957 2.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1297 2.7325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9957 1.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2637 2.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1297 0.7325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2204 -1.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8913 4.3634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7784 0.6988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 4.8140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3977 0.7325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2819 -2.6715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3913 3.4974 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1122 4.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3308 1.5324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1612 5.2320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0540 -1.1210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9622 0.1210 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4434 4.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2637 1.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5316 1.2325 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5447 2.5092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1593 5.2935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9924 -0.1229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8332 3.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8810 0.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8640 2.1757 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5442 2.4785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2822 6.2859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8100 3.3891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5079 -0.3060 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 10 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 9 28 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 29 2 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 22 1 0 0 0 0 17 23 2 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 20 29 1 0 0 0 0 21 2 1 6 0 0 0 22 3 1 1 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 31 1 0 0 0 0 25 6 1 1 0 0 0 25 32 1 0 0 0 0 26 7 1 6 0 0 0 27 8 1 1 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 30 20 1 1 0 0 0 30 35 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 1 0 0 0 32 38 1 6 0 0 0 33 26 1 6 0 0 0 33 41 1 0 0 0 0 34 36 2 3 0 0 0 34 39 1 0 0 0 0 35 40 2 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	567.39
Volume:	630.659
LogP:	5.435
LogD:	5.539
LogS:	-5.442
# Rotatable Bonds:	6
TPSA:	96.19
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	5.438
Fsp3:	0.629
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.788
MDCK Permeability:	1.5984887795639224e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.886
Human Intestinal Absorption (HIA):	0.826
20% Bioavailability (F20%):	0.467
30% Bioavailability (F30%):	0.081

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	98.64055633544922%
Volume Distribution (VD):	1.294
Pgp-substrate:	1.8192224502563477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.22
CYP2C19-substrate:	0.409
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	8.913
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.091
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC190663

Natural Product ID:	NPC190663
*Common Name:**	Metacridamide B
IUPAC Name:	(3S,6E,8S,9R,10E,12S,13S,14E,16S,17R)-3-benzyl-9,13-dihydroxy-6,8,10,12,14,16-hexamethyl-17-[(2S,4S)-4-methylhexan-2-yl]-1-oxa-4-azacycloheptadeca-6,10,14-triene-2,5-dione
Synonyms:	Metacridamide B
Standard InCHIKey:	GBWYSPYPUUAVKR-MCSORCGTSA-N
Standard InCHI:	InChI=1S/C35H53NO5/c1-10-21(2)16-26(7)33-27(8)18-24(5)31(37)22(3)17-23(4)32(38)25(6)19-28(9)34(39)36-30(35(40)41-33)20-29-14-12-11-13-15-29/h11-15,17-19,21-22,25-27,30-33,37-38H,10,16,20H2,1-9H3,(H,36,39)/b23-17+,24-18+,28-19+/t21-,22-,25-,26-,27-,30-,31-,32-,33+/m0/s1
SMILES:	CC[C@H](C)C[C@H](C)[C@@H]1[C@@H](C)/C=C(C)/[C@H]([C@@H](C)/C=C(C)/[C@@H]([C@@H](C)/C=C(C)/C(=N[C@@H](Cc2ccccc2)C(=O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011790
PubChem CID:	57332101
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276742]
NPO17498	Metarhizium acridum	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22292922]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28290701]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17498	Metarhizium acridum	Species	Clavicipitaceae	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18200.0	nM	PMID[492341]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18200.0	nM	PMID[492342]

☑ 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 NPC190663 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	93
0.1-0.2	483
0.2-0.3	2040
0.3-0.4	7378
0.4-0.5	21827
0.5-0.6	9124
0.6-0.7	1418
0.7-0.8	297
0.8-0.85	26
0.85-0.9	4
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC160493
0.9145	High Similarity	NPC80150
0.9138	High Similarity	NPC310467
0.9052	High Similarity	NPC169328
0.8655	High Similarity	NPC237420
0.8512	High Similarity	NPC478014
0.8512	High Similarity	NPC478016
0.8512	High Similarity	NPC478015
0.8468	Intermediate Similarity	NPC4974
0.8413	Intermediate Similarity	NPC296712
0.8361	Intermediate Similarity	NPC477061
0.8361	Intermediate Similarity	NPC45777
0.8333	Intermediate Similarity	NPC210950
0.8333	Intermediate Similarity	NPC199738
0.832	Intermediate Similarity	NPC47667
0.8305	Intermediate Similarity	NPC273814
0.8151	Intermediate Similarity	NPC474584
0.8134	Intermediate Similarity	NPC91953
0.8065	Intermediate Similarity	NPC476183
0.806	Intermediate Similarity	NPC197921
0.8053	Intermediate Similarity	NPC12730
0.8049	Intermediate Similarity	NPC314992
0.8016	Intermediate Similarity	NPC35996
0.8	Intermediate Similarity	NPC476184
0.8	Intermediate Similarity	NPC476281
0.797	Intermediate Similarity	NPC6570
0.7953	Intermediate Similarity	NPC476241
0.7953	Intermediate Similarity	NPC476260
0.7951	Intermediate Similarity	NPC197470
0.7937	Intermediate Similarity	NPC474862
0.7899	Intermediate Similarity	NPC135121
0.7891	Intermediate Similarity	NPC476125
0.7891	Intermediate Similarity	NPC476179
0.7886	Intermediate Similarity	NPC2265
0.7874	Intermediate Similarity	NPC476278
0.7868	Intermediate Similarity	NPC469360
0.781	Intermediate Similarity	NPC476978
0.7803	Intermediate Similarity	NPC246913
0.7803	Intermediate Similarity	NPC246079
0.7797	Intermediate Similarity	NPC327481
0.7794	Intermediate Similarity	NPC269398
0.7794	Intermediate Similarity	NPC263493
0.7778	Intermediate Similarity	NPC194390
0.7778	Intermediate Similarity	NPC224610
0.7778	Intermediate Similarity	NPC88267
0.7778	Intermediate Similarity	NPC113326
0.7769	Intermediate Similarity	NPC476353
0.7754	Intermediate Similarity	NPC201244
0.7754	Intermediate Similarity	NPC477217
0.7737	Intermediate Similarity	NPC139326
0.7737	Intermediate Similarity	NPC161069
0.7721	Intermediate Similarity	NPC471201
0.7721	Intermediate Similarity	NPC322526
0.771	Intermediate Similarity	NPC472413
0.7699	Intermediate Similarity	NPC58674
0.7698	Intermediate Similarity	NPC319950
0.7692	Intermediate Similarity	NPC164859
0.7686	Intermediate Similarity	NPC323007
0.7686	Intermediate Similarity	NPC319579
0.7669	Intermediate Similarity	NPC45191
0.7661	Intermediate Similarity	NPC188010
0.7656	Intermediate Similarity	NPC142577
0.7652	Intermediate Similarity	NPC478147
0.7647	Intermediate Similarity	NPC191215
0.7647	Intermediate Similarity	NPC274089
0.7647	Intermediate Similarity	NPC473055
0.7647	Intermediate Similarity	NPC473052
0.7626	Intermediate Similarity	NPC5620
0.7623	Intermediate Similarity	NPC329011
0.7615	Intermediate Similarity	NPC472414
0.7612	Intermediate Similarity	NPC244866
0.7612	Intermediate Similarity	NPC470392
0.7612	Intermediate Similarity	NPC328070
0.7597	Intermediate Similarity	NPC472415
0.7594	Intermediate Similarity	NPC183722
0.7591	Intermediate Similarity	NPC268841
0.7591	Intermediate Similarity	NPC163392
0.7591	Intermediate Similarity	NPC239762
0.7591	Intermediate Similarity	NPC307357
0.7591	Intermediate Similarity	NPC46098
0.7576	Intermediate Similarity	NPC116057
0.7574	Intermediate Similarity	NPC471265
0.7574	Intermediate Similarity	NPC471264
0.7574	Intermediate Similarity	NPC127741
0.7571	Intermediate Similarity	NPC314358
0.7565	Intermediate Similarity	NPC473501
0.7565	Intermediate Similarity	NPC475439
0.7563	Intermediate Similarity	NPC211551
0.7556	Intermediate Similarity	NPC64897
0.7556	Intermediate Similarity	NPC90693
0.7552	Intermediate Similarity	NPC470274
0.7542	Intermediate Similarity	NPC471317
0.7536	Intermediate Similarity	NPC239770
0.7521	Intermediate Similarity	NPC114741
0.7521	Intermediate Similarity	NPC182549
0.7519	Intermediate Similarity	NPC84281
0.7519	Intermediate Similarity	NPC317474
0.7519	Intermediate Similarity	NPC291027
0.7519	Intermediate Similarity	NPC169485
0.7519	Intermediate Similarity	NPC213126
0.7518	Intermediate Similarity	NPC470884
0.7518	Intermediate Similarity	NPC225648
0.7518	Intermediate Similarity	NPC329761
0.7518	Intermediate Similarity	NPC98424
0.7518	Intermediate Similarity	NPC178662
0.7518	Intermediate Similarity	NPC92784
0.7518	Intermediate Similarity	NPC476133
0.7518	Intermediate Similarity	NPC138775
0.75	Intermediate Similarity	NPC209509
0.75	Intermediate Similarity	NPC474544
0.75	Intermediate Similarity	NPC313867
0.75	Intermediate Similarity	NPC1986
0.75	Intermediate Similarity	NPC316008
0.7483	Intermediate Similarity	NPC475168
0.7483	Intermediate Similarity	NPC7817
0.7478	Intermediate Similarity	NPC25565
0.7447	Intermediate Similarity	NPC81026
0.7445	Intermediate Similarity	NPC68865
0.7445	Intermediate Similarity	NPC208725
0.7444	Intermediate Similarity	NPC71271
0.7429	Intermediate Similarity	NPC315283
0.7429	Intermediate Similarity	NPC314388
0.7424	Intermediate Similarity	NPC65310
0.7414	Intermediate Similarity	NPC293628
0.7414	Intermediate Similarity	NPC10781
0.7414	Intermediate Similarity	NPC122493
0.7413	Intermediate Similarity	NPC132771
0.7413	Intermediate Similarity	NPC2501
0.7413	Intermediate Similarity	NPC129666
0.7407	Intermediate Similarity	NPC326966
0.7394	Intermediate Similarity	NPC145113
0.7388	Intermediate Similarity	NPC325651
0.7388	Intermediate Similarity	NPC69496
0.7385	Intermediate Similarity	NPC27581
0.7379	Intermediate Similarity	NPC473341
0.7376	Intermediate Similarity	NPC266741
0.7368	Intermediate Similarity	NPC89923
0.7368	Intermediate Similarity	NPC239990
0.7368	Intermediate Similarity	NPC105114
0.7368	Intermediate Similarity	NPC152850
0.7368	Intermediate Similarity	NPC71933
0.7357	Intermediate Similarity	NPC197682
0.7355	Intermediate Similarity	NPC477251
0.7353	Intermediate Similarity	NPC233910
0.7353	Intermediate Similarity	NPC245836
0.735	Intermediate Similarity	NPC322598
0.7348	Intermediate Similarity	NPC474847
0.7343	Intermediate Similarity	NPC105717
0.7329	Intermediate Similarity	NPC470902
0.7329	Intermediate Similarity	NPC39431
0.7328	Intermediate Similarity	NPC3371
0.7311	Intermediate Similarity	NPC318154
0.731	Intermediate Similarity	NPC162104
0.7305	Intermediate Similarity	NPC52748
0.7297	Intermediate Similarity	NPC56635
0.7293	Intermediate Similarity	NPC136453
0.7293	Intermediate Similarity	NPC477937
0.7286	Intermediate Similarity	NPC469426
0.7286	Intermediate Similarity	NPC469427
0.7286	Intermediate Similarity	NPC168113
0.7279	Intermediate Similarity	NPC42423
0.7273	Intermediate Similarity	NPC67043
0.7265	Intermediate Similarity	NPC324569
0.726	Intermediate Similarity	NPC122590
0.7254	Intermediate Similarity	NPC473922
0.7246	Intermediate Similarity	NPC279045
0.7246	Intermediate Similarity	NPC113325
0.7239	Intermediate Similarity	NPC319766
0.7234	Intermediate Similarity	NPC111586
0.7234	Intermediate Similarity	NPC57976
0.7234	Intermediate Similarity	NPC176226
0.7234	Intermediate Similarity	NPC261709
0.7234	Intermediate Similarity	NPC108852
0.7227	Intermediate Similarity	NPC469457
0.7227	Intermediate Similarity	NPC228400
0.7227	Intermediate Similarity	NPC214200
0.7226	Intermediate Similarity	NPC313663
0.7222	Intermediate Similarity	NPC471820
0.7222	Intermediate Similarity	NPC471821
0.7222	Intermediate Similarity	NPC35850
0.7222	Intermediate Similarity	NPC276949
0.7219	Intermediate Similarity	NPC471053
0.7219	Intermediate Similarity	NPC471052
0.7219	Intermediate Similarity	NPC471051
0.7218	Intermediate Similarity	NPC101719
0.7214	Intermediate Similarity	NPC476259
0.7209	Intermediate Similarity	NPC470546
0.7206	Intermediate Similarity	NPC157311
0.7203	Intermediate Similarity	NPC262077
0.7203	Intermediate Similarity	NPC262216
0.72	Intermediate Similarity	NPC476194
0.7197	Intermediate Similarity	NPC46427
0.7197	Intermediate Similarity	NPC6975
0.7193	Intermediate Similarity	NPC258627
0.719	Intermediate Similarity	NPC19136
0.7185	Intermediate Similarity	NPC165726
0.7185	Intermediate Similarity	NPC213969
0.7185	Intermediate Similarity	NPC469666
0.7181	Intermediate Similarity	NPC93343
0.7181	Intermediate Similarity	NPC212699

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 NPC190663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	324
0.2-0.3	786
0.3-0.4	1980
0.4-0.5	3271
0.5-0.6	2023
0.6-0.7	565
0.7-0.8	112
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.814	Intermediate Similarity	NPD4738	Phase 2
0.8136	Intermediate Similarity	NPD3642	Approved
0.8136	Intermediate Similarity	NPD3644	Approved
0.8136	Intermediate Similarity	NPD3643	Approved
0.8049	Intermediate Similarity	NPD2217	Approved
0.8049	Intermediate Similarity	NPD2218	Phase 2
0.7984	Intermediate Similarity	NPD5981	Approved
0.7951	Intermediate Similarity	NPD1348	Approved
0.7874	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3136	Phase 2
0.76	Intermediate Similarity	NPD3123	Discovery
0.7597	Intermediate Similarity	NPD2584	Suspended
0.7559	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2611	Approved
0.7519	Intermediate Similarity	NPD2609	Approved
0.7519	Intermediate Similarity	NPD2608	Approved
0.7519	Intermediate Similarity	NPD2610	Approved
0.7519	Intermediate Similarity	NPD4215	Approved
0.7519	Intermediate Similarity	NPD4806	Approved
0.7519	Intermediate Similarity	NPD4217	Approved
0.7519	Intermediate Similarity	NPD4218	Approved
0.7519	Intermediate Similarity	NPD3132	Approved
0.7519	Intermediate Similarity	NPD2612	Approved
0.7519	Intermediate Similarity	NPD3131	Approved
0.7519	Intermediate Similarity	NPD4807	Approved
0.7519	Intermediate Similarity	NPD4216	Approved
0.7518	Intermediate Similarity	NPD6852	Discontinued
0.75	Intermediate Similarity	NPD2650	Approved
0.75	Intermediate Similarity	NPD2652	Approved
0.7481	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD4479	Discontinued
0.7462	Intermediate Similarity	NPD6624	Discontinued
0.7445	Intermediate Similarity	NPD8172	Phase 2
0.7445	Intermediate Similarity	NPD8173	Phase 2
0.7424	Intermediate Similarity	NPD2159	Approved
0.7424	Intermediate Similarity	NPD2160	Approved
0.7424	Intermediate Similarity	NPD2627	Approved
0.7424	Intermediate Similarity	NPD2628	Approved
0.7424	Intermediate Similarity	NPD2626	Approved
0.7424	Intermediate Similarity	NPD2625	Approved
0.7417	Intermediate Similarity	NPD1040	Phase 2
0.7414	Intermediate Similarity	NPD9566	Approved
0.7402	Intermediate Similarity	NPD1758	Phase 1
0.7395	Intermediate Similarity	NPD6647	Phase 2
0.7394	Intermediate Similarity	NPD8323	Discontinued
0.7388	Intermediate Similarity	NPD2613	Approved
0.7388	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7978	Discontinued
0.7353	Intermediate Similarity	NPD3088	Approved
0.7353	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4746	Phase 3
0.7353	Intermediate Similarity	NPD3087	Approved
0.7353	Intermediate Similarity	NPD3090	Approved
0.7353	Intermediate Similarity	NPD2570	Approved
0.7353	Intermediate Similarity	NPD2573	Approved
0.7353	Intermediate Similarity	NPD2574	Discontinued
0.7353	Intermediate Similarity	NPD4745	Approved
0.7353	Intermediate Similarity	NPD3089	Approved
0.7353	Intermediate Similarity	NPD2571	Approved
0.7353	Intermediate Similarity	NPD2566	Approved
0.7353	Intermediate Similarity	NPD3614	Approved
0.7353	Intermediate Similarity	NPD3615	Approved
0.7353	Intermediate Similarity	NPD3616	Approved
0.7348	Intermediate Similarity	NPD6325	Discontinued
0.7344	Intermediate Similarity	NPD1759	Phase 1
0.7338	Intermediate Similarity	NPD6865	Phase 2
0.7338	Intermediate Similarity	NPD6864	Phase 2
0.7323	Intermediate Similarity	NPD4574	Approved
0.7323	Intermediate Similarity	NPD4576	Approved
0.7313	Intermediate Similarity	NPD3662	Phase 3
0.7313	Intermediate Similarity	NPD3661	Approved
0.7313	Intermediate Similarity	NPD3663	Approved
0.7313	Intermediate Similarity	NPD3664	Approved
0.731	Intermediate Similarity	NPD6390	Discontinued
0.7308	Intermediate Similarity	NPD4136	Approved
0.7308	Intermediate Similarity	NPD4106	Approved
0.7308	Intermediate Similarity	NPD4135	Approved
0.7299	Intermediate Similarity	NPD8265	Approved
0.7295	Intermediate Similarity	NPD6406	Approved
0.7287	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2607	Approved
0.7279	Intermediate Similarity	NPD4621	Approved
0.7279	Intermediate Similarity	NPD4619	Approved
0.7259	Intermediate Similarity	NPD5201	Approved
0.7259	Intermediate Similarity	NPD4617	Approved
0.7259	Intermediate Similarity	NPD5203	Approved
0.7259	Intermediate Similarity	NPD4620	Approved
0.7252	Intermediate Similarity	NPD4480	Approved
0.7252	Intermediate Similarity	NPD3603	Phase 3
0.7252	Intermediate Similarity	NPD5618	Discontinued
0.7246	Intermediate Similarity	NPD4685	Phase 3
0.7246	Intermediate Similarity	NPD4684	Phase 3
0.7246	Intermediate Similarity	NPD4686	Approved
0.7241	Intermediate Similarity	NPD4814	Discontinued
0.7231	Intermediate Similarity	NPD5305	Approved
0.7231	Intermediate Similarity	NPD5306	Approved
0.7227	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7714	Approved
0.7226	Intermediate Similarity	NPD7715	Approved
0.7206	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5204	Approved
0.7185	Intermediate Similarity	NPD7828	Discontinued
0.7183	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5121	Approved
0.7174	Intermediate Similarity	NPD8416	Discontinued
0.7174	Intermediate Similarity	NPD5119	Approved
0.7174	Intermediate Similarity	NPD5120	Approved
0.7167	Intermediate Similarity	NPD854	Approved
0.7167	Intermediate Similarity	NPD855	Approved
0.7164	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4102	Approved
0.7154	Intermediate Similarity	NPD4105	Approved
0.7143	Intermediate Similarity	NPD9712	Approved
0.7107	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3125	Approved
0.7083	Intermediate Similarity	NPD2575	Approved
0.7083	Intermediate Similarity	NPD3400	Discontinued
0.7077	Intermediate Similarity	NPD6093	Discontinued
0.7077	Intermediate Similarity	NPD2617	Discontinued
0.7073	Intermediate Similarity	NPD5706	Approved
0.7073	Intermediate Similarity	NPD5705	Approved
0.7073	Intermediate Similarity	NPD467	Phase 1
0.7073	Intermediate Similarity	NPD5704	Approved
0.7069	Intermediate Similarity	NPD6690	Approved
0.7067	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6913	Approved
0.7059	Intermediate Similarity	NPD253	Approved
0.7059	Intermediate Similarity	NPD9710	Approved
0.7059	Intermediate Similarity	NPD9612	Approved
0.7059	Intermediate Similarity	NPD9609	Approved
0.7059	Intermediate Similarity	NPD9611	Approved
0.7059	Intermediate Similarity	NPD9711	Approved
0.7054	Intermediate Similarity	NPD9568	Approved
0.7045	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4234	Approved
0.704	Intermediate Similarity	NPD4233	Approved
0.7034	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2629	Approved
0.7015	Intermediate Similarity	NPD5159	Phase 2
0.7015	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5157	Phase 1
0.7009	Intermediate Similarity	NPD1066	Discontinued
0.7007	Intermediate Similarity	NPD4125	Approved
0.7	Intermediate Similarity	NPD6065	Approved
0.7	Intermediate Similarity	NPD555	Phase 2
0.7	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5048	Discontinued
0.6985	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7508	Discontinued
0.6977	Remote Similarity	NPD255	Approved
0.6977	Remote Similarity	NPD256	Approved
0.6974	Remote Similarity	NPD7972	Discontinued
0.6963	Remote Similarity	NPD2198	Approved
0.6963	Remote Similarity	NPD3098	Discontinued
0.6963	Remote Similarity	NPD2199	Approved
0.6957	Remote Similarity	NPD5347	Phase 2
0.6957	Remote Similarity	NPD5346	Phase 2
0.6953	Remote Similarity	NPD1371	Approved
0.6953	Remote Similarity	NPD1373	Approved
0.6953	Remote Similarity	NPD1374	Approved
0.6953	Remote Similarity	NPD1370	Approved
0.6944	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6681	Discovery
0.6935	Remote Similarity	NPD6685	Approved
0.6934	Remote Similarity	NPD4175	Approved
0.6934	Remote Similarity	NPD3626	Phase 3
0.6934	Remote Similarity	NPD4177	Approved
0.6929	Remote Similarity	NPD825	Approved
0.6929	Remote Similarity	NPD6311	Approved
0.6929	Remote Similarity	NPD826	Approved
0.6929	Remote Similarity	NPD6310	Approved
0.6929	Remote Similarity	NPD6309	Approved
0.6923	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5291	Approved
0.6923	Remote Similarity	NPD4173	Approved
0.6923	Remote Similarity	NPD4172	Approved
0.6923	Remote Similarity	NPD5292	Approved
0.6917	Remote Similarity	NPD9495	Approved
0.6913	Remote Similarity	NPD7131	Phase 3
0.6911	Remote Similarity	NPD10	Approved
0.6911	Remote Similarity	NPD310	Approved
0.6911	Remote Similarity	NPD309	Approved
0.6911	Remote Similarity	NPD314	Approved
0.6911	Remote Similarity	NPD311	Approved
0.6911	Remote Similarity	NPD315	Approved
0.6908	Remote Similarity	NPD8019	Approved
0.6905	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1752	Approved
0.6905	Remote Similarity	NPD1756	Approved
0.6897	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3673	Approved
0.6897	Remote Similarity	NPD3672	Approved
0.6892	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8417	Discontinued
0.6879	Remote Similarity	NPD8643	Discontinued
0.6875	Remote Similarity	NPD4152	Approved
0.687	Remote Similarity	NPD7522	Discontinued
0.6864	Remote Similarity	NPD5122	Clinical (unspecified phase)

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