NPASS Compound

Structure

NPC146822 OpenBabel07101718332D 44 46 0 0 1 0 0 0 0 0999 V2000 -3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 2.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.2321 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0981 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 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 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5981 1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0345 3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 32 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 9 42 1 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 13 1 0 0 0 0 11 26 2 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 27 2 0 0 0 0 16 19 1 0 0 0 0 16 30 1 0 0 0 0 17 34 1 0 0 0 0 18 33 1 0 0 0 0 20 35 1 0 0 0 0 20 43 1 0 0 0 0 21 31 1 0 0 0 0 22 2 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 36 2 0 0 0 0 23 43 1 0 0 0 0 24 37 2 0 0 0 0 24 44 1 0 0 0 0 25 33 1 6 0 0 0 26 27 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 12 1 1 0 0 0 28 44 1 0 0 0 0 29 32 1 0 0 0 0 29 35 1 6 0 0 0 30 38 2 0 0 0 0 30 42 1 0 0 0 0 31 39 2 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 33 34 1 6 0 0 0 34 8 1 1 0 0 0 35 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.36
Volume:	648.903
LogP:	4.146
LogD:	2.611
LogS:	-3.94
# Rotatable Bonds:	15
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	5.461
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
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:	-5.192
MDCK Permeability:	3.6173983971821144e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.3
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	91.11479187011719%
Volume Distribution (VD):	0.719
Pgp-substrate:	3.401254177093506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.187
CYP2C9-substrate:	0.155
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	1.94
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.627
Skin Sensitization:	0.335
Carcinogencity:	0.352
Eye Corrosion:	0.027
Eye Irritation:	0.042
Respiratory Toxicity:	0.552

Download Data

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

Natural Product: NPC146822

Natural Product ID:	NPC146822
*Common Name:**	Colossolactone Vi
IUPAC Name:	(Z,5R,6S)-6-[(3R,3aR,6R,7R,9bR)-6-(acetyloxymethyl)-7-(2-hydroxypropan-2-yl)-6-(3-methoxy-3-oxopropyl)-3a,9b-dimethyl-1,2,3,4,7,8-hexahydrocyclopenta[a]naphthalen-3-yl]-5-acetyloxy-2-methylhept-2-enoic acid
Synonyms:	colossolactone VI
Standard InCHIKey:	IQKAWHUEZWYQHM-SGTCUYSDSA-N
Standard InCHI:	InChI=1S/C35H52O9/c1-21(31(39)40)10-12-28(44-24(4)37)22(2)25-14-17-34(8)26-11-13-29(32(5,6)41)35(20-43-23(3)36,19-16-30(38)42-9)27(26)15-18-33(25,34)7/h10-11,15,22,25,28-29,41H,12-14,16-20H2,1-9H3,(H,39,40)/b21-10-/t22-,25+,28+,29-,33+,34-,35-/m0/s1
SMILES:	C/C(=C/C[C@H]([C@@H](C)[C@H]1CC[C@@]2(C)C3=CC[C@@H](C(C)(C)O)[C@@](CCC(=O)OC)(COC(=O)C)C3=CC[C@]12C)OC(=O)C)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446797
PubChem CID:	24898245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	vietnamese	n.a.	PMID[18547117]
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547117]
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19813754]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	>	100.0	ug.mL-1	PMID[530733]

☑ 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 NPC146822 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	192
0.1-0.2	1002
0.2-0.3	4061
0.3-0.4	9073
0.4-0.5	13515
0.5-0.6	7522
0.6-0.7	5918
0.7-0.8	1337
0.8-0.85	57
0.85-0.9	7
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9681	High Similarity	NPC241221
0.9082	High Similarity	NPC475320
0.8788	High Similarity	NPC99411
0.8557	High Similarity	NPC7165
0.8485	Intermediate Similarity	NPC469432
0.8447	Intermediate Similarity	NPC472935
0.8431	Intermediate Similarity	NPC85742
0.84	Intermediate Similarity	NPC235464
0.84	Intermediate Similarity	NPC166745
0.8351	Intermediate Similarity	NPC45269
0.8317	Intermediate Similarity	NPC476274
0.83	Intermediate Similarity	NPC141401
0.83	Intermediate Similarity	NPC202705
0.8283	Intermediate Similarity	NPC20546
0.828	Intermediate Similarity	NPC310470
0.8247	Intermediate Similarity	NPC477147
0.8247	Intermediate Similarity	NPC123854
0.8247	Intermediate Similarity	NPC477149
0.8241	Intermediate Similarity	NPC472926
0.8235	Intermediate Similarity	NPC476223
0.8235	Intermediate Similarity	NPC476240
0.8235	Intermediate Similarity	NPC224720
0.8218	Intermediate Similarity	NPC471717
0.8218	Intermediate Similarity	NPC197386
0.82	Intermediate Similarity	NPC328371
0.8182	Intermediate Similarity	NPC472934
0.8172	Intermediate Similarity	NPC296367
0.8163	Intermediate Similarity	NPC474018
0.8163	Intermediate Similarity	NPC473986
0.8163	Intermediate Similarity	NPC204341
0.8163	Intermediate Similarity	NPC470113
0.8155	Intermediate Similarity	NPC235369
0.8155	Intermediate Similarity	NPC308726
0.8155	Intermediate Similarity	NPC119601
0.8148	Intermediate Similarity	NPC236217
0.8144	Intermediate Similarity	NPC214387
0.8137	Intermediate Similarity	NPC266955
0.8131	Intermediate Similarity	NPC473627
0.81	Intermediate Similarity	NPC174948
0.81	Intermediate Similarity	NPC171395
0.81	Intermediate Similarity	NPC173875
0.81	Intermediate Similarity	NPC469995
0.81	Intermediate Similarity	NPC318282
0.8077	Intermediate Similarity	NPC280566
0.8077	Intermediate Similarity	NPC236390
0.8077	Intermediate Similarity	NPC72151
0.8058	Intermediate Similarity	NPC115899
0.8058	Intermediate Similarity	NPC472924
0.8058	Intermediate Similarity	NPC302537
0.8058	Intermediate Similarity	NPC163372
0.8041	Intermediate Similarity	NPC472870
0.8041	Intermediate Similarity	NPC247406
0.8041	Intermediate Similarity	NPC48866
0.8037	Intermediate Similarity	NPC304495
0.8036	Intermediate Similarity	NPC472933
0.802	Intermediate Similarity	NPC42042
0.802	Intermediate Similarity	NPC456
0.802	Intermediate Similarity	NPC472941
0.802	Intermediate Similarity	NPC155676
0.8019	Intermediate Similarity	NPC475294
0.8018	Intermediate Similarity	NPC472927
0.8	Intermediate Similarity	NPC184870
0.8	Intermediate Similarity	NPC164577
0.8	Intermediate Similarity	NPC474181
0.8	Intermediate Similarity	NPC469406
0.7982	Intermediate Similarity	NPC221144
0.7981	Intermediate Similarity	NPC195290
0.7981	Intermediate Similarity	NPC204450
0.7981	Intermediate Similarity	NPC475558
0.7981	Intermediate Similarity	NPC56498
0.7981	Intermediate Similarity	NPC136289
0.7981	Intermediate Similarity	NPC473788
0.7981	Intermediate Similarity	NPC320447
0.798	Intermediate Similarity	NPC26888
0.798	Intermediate Similarity	NPC472705
0.7963	Intermediate Similarity	NPC37116
0.7963	Intermediate Similarity	NPC197428
0.7961	Intermediate Similarity	NPC471041
0.7961	Intermediate Similarity	NPC290802
0.7961	Intermediate Similarity	NPC287833
0.7959	Intermediate Similarity	NPC123912
0.7959	Intermediate Similarity	NPC155479
0.7959	Intermediate Similarity	NPC310236
0.7944	Intermediate Similarity	NPC472218
0.7944	Intermediate Similarity	NPC472217
0.7944	Intermediate Similarity	NPC472219
0.7944	Intermediate Similarity	NPC220155
0.7941	Intermediate Similarity	NPC320306
0.7941	Intermediate Similarity	NPC18319
0.7938	Intermediate Similarity	NPC128644
0.7928	Intermediate Similarity	NPC190286
0.7928	Intermediate Similarity	NPC176840
0.7928	Intermediate Similarity	NPC148458
0.7925	Intermediate Similarity	NPC323834
0.7921	Intermediate Similarity	NPC293052
0.7909	Intermediate Similarity	NPC469463
0.7909	Intermediate Similarity	NPC469496
0.7909	Intermediate Similarity	NPC962
0.7909	Intermediate Similarity	NPC469454
0.7909	Intermediate Similarity	NPC472929
0.7905	Intermediate Similarity	NPC183570
0.79	Intermediate Similarity	NPC214697
0.79	Intermediate Similarity	NPC38232
0.79	Intermediate Similarity	NPC476416
0.7895	Intermediate Similarity	NPC97913
0.7895	Intermediate Similarity	NPC202051
0.789	Intermediate Similarity	NPC304180
0.789	Intermediate Similarity	NPC179798
0.789	Intermediate Similarity	NPC471484
0.789	Intermediate Similarity	NPC262083
0.7885	Intermediate Similarity	NPC469657
0.7885	Intermediate Similarity	NPC118174
0.7885	Intermediate Similarity	NPC81530
0.7885	Intermediate Similarity	NPC244456
0.7879	Intermediate Similarity	NPC46281
0.7879	Intermediate Similarity	NPC175628
0.7879	Intermediate Similarity	NPC111585
0.7879	Intermediate Similarity	NPC472866
0.7879	Intermediate Similarity	NPC148414
0.7876	Intermediate Similarity	NPC270850
0.7876	Intermediate Similarity	NPC5292
0.7876	Intermediate Similarity	NPC305260
0.787	Intermediate Similarity	NPC475274
0.7864	Intermediate Similarity	NPC98868
0.7864	Intermediate Similarity	NPC23364
0.7864	Intermediate Similarity	NPC48647
0.7864	Intermediate Similarity	NPC477813
0.7864	Intermediate Similarity	NPC186810
0.7857	Intermediate Similarity	NPC193843
0.7857	Intermediate Similarity	NPC117122
0.7857	Intermediate Similarity	NPC183546
0.7857	Intermediate Similarity	NPC249889
0.7857	Intermediate Similarity	NPC294480
0.785	Intermediate Similarity	NPC473284
0.785	Intermediate Similarity	NPC91034
0.785	Intermediate Similarity	NPC472925
0.7849	Intermediate Similarity	NPC274996
0.7849	Intermediate Similarity	NPC196827
0.7843	Intermediate Similarity	NPC7124
0.7843	Intermediate Similarity	NPC301534
0.7843	Intermediate Similarity	NPC250757
0.7838	Intermediate Similarity	NPC305044
0.7838	Intermediate Similarity	NPC265290
0.7835	Intermediate Similarity	NPC472869
0.783	Intermediate Similarity	NPC472868
0.783	Intermediate Similarity	NPC309190
0.783	Intermediate Similarity	NPC272632
0.783	Intermediate Similarity	NPC118911
0.7822	Intermediate Similarity	NPC90453
0.7822	Intermediate Similarity	NPC474922
0.7818	Intermediate Similarity	NPC100267
0.7818	Intermediate Similarity	NPC170487
0.7818	Intermediate Similarity	NPC475524
0.7818	Intermediate Similarity	NPC241477
0.7812	Intermediate Similarity	NPC165064
0.7812	Intermediate Similarity	NPC472865
0.781	Intermediate Similarity	NPC155332
0.781	Intermediate Similarity	NPC469606
0.781	Intermediate Similarity	NPC22388
0.781	Intermediate Similarity	NPC32577
0.781	Intermediate Similarity	NPC162973
0.781	Intermediate Similarity	NPC293753
0.781	Intermediate Similarity	NPC66110
0.781	Intermediate Similarity	NPC114540
0.781	Intermediate Similarity	NPC273005
0.781	Intermediate Similarity	NPC31058
0.78	Intermediate Similarity	NPC221282
0.78	Intermediate Similarity	NPC212948
0.7798	Intermediate Similarity	NPC181298
0.7798	Intermediate Similarity	NPC129689
0.7798	Intermediate Similarity	NPC238850
0.7788	Intermediate Similarity	NPC167974
0.7788	Intermediate Similarity	NPC470074
0.7788	Intermediate Similarity	NPC471413
0.7788	Intermediate Similarity	NPC475913
0.7788	Intermediate Similarity	NPC218383
0.7788	Intermediate Similarity	NPC153440
0.7788	Intermediate Similarity	NPC51370
0.7788	Intermediate Similarity	NPC327431
0.7788	Intermediate Similarity	NPC227865
0.7788	Intermediate Similarity	NPC205899
0.7778	Intermediate Similarity	NPC66344
0.7778	Intermediate Similarity	NPC262043
0.7778	Intermediate Similarity	NPC118011
0.7778	Intermediate Similarity	NPC284561
0.7778	Intermediate Similarity	NPC295244
0.7778	Intermediate Similarity	NPC36668
0.7778	Intermediate Similarity	NPC474889
0.7768	Intermediate Similarity	NPC49492
0.7768	Intermediate Similarity	NPC266728
0.7767	Intermediate Similarity	NPC107243
0.7767	Intermediate Similarity	NPC121339
0.7767	Intermediate Similarity	NPC170131
0.7767	Intermediate Similarity	NPC99726
0.7757	Intermediate Similarity	NPC181265
0.7757	Intermediate Similarity	NPC469607
0.7755	Intermediate Similarity	NPC312215
0.7755	Intermediate Similarity	NPC167877
0.7755	Intermediate Similarity	NPC136948
0.7755	Intermediate Similarity	NPC312561

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 NPC146822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1409
0.2-0.3	3596
0.3-0.4	2576
0.4-0.5	879
0.5-0.6	265
0.6-0.7	243
0.7-0.8	21
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
0.7723	Intermediate Similarity	NPD6399	Phase 3
0.7624	Intermediate Similarity	NPD5281	Approved
0.7624	Intermediate Similarity	NPD5284	Approved
0.7573	Intermediate Similarity	NPD5695	Phase 3
0.7549	Intermediate Similarity	NPD5778	Approved
0.7549	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD6899	Approved
0.7455	Intermediate Similarity	NPD6881	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7451	Intermediate Similarity	NPD6050	Approved
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7429	Intermediate Similarity	NPD6083	Phase 2
0.7429	Intermediate Similarity	NPD6084	Phase 2
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD8130	Phase 1
0.7411	Intermediate Similarity	NPD6649	Approved
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD5697	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7353	Intermediate Similarity	NPD5692	Phase 3
0.7345	Intermediate Similarity	NPD6882	Approved
0.7327	Intermediate Similarity	NPD6672	Approved
0.7327	Intermediate Similarity	NPD5737	Approved
0.7321	Intermediate Similarity	NPD7102	Approved
0.7321	Intermediate Similarity	NPD7290	Approved
0.7321	Intermediate Similarity	NPD6883	Approved
0.73	Intermediate Similarity	NPD6684	Approved
0.73	Intermediate Similarity	NPD7334	Approved
0.73	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD7521	Approved
0.73	Intermediate Similarity	NPD6409	Approved
0.73	Intermediate Similarity	NPD5279	Phase 3
0.73	Intermediate Similarity	NPD5330	Approved
0.7297	Intermediate Similarity	NPD7320	Approved
0.7297	Intermediate Similarity	NPD6011	Approved
0.729	Intermediate Similarity	NPD6404	Discontinued
0.7282	Intermediate Similarity	NPD7637	Suspended
0.7282	Intermediate Similarity	NPD7983	Approved
0.7282	Intermediate Similarity	NPD5694	Approved
0.7282	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD6008	Approved
0.7257	Intermediate Similarity	NPD6617	Approved
0.7257	Intermediate Similarity	NPD6869	Approved
0.7257	Intermediate Similarity	NPD6847	Approved
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD6014	Approved
0.7232	Intermediate Similarity	NPD6013	Approved
0.7232	Intermediate Similarity	NPD6012	Approved
0.7207	Intermediate Similarity	NPD5701	Approved
0.7196	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5696	Approved
0.7188	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5785	Approved
0.7184	Intermediate Similarity	NPD5207	Approved
0.7177	Intermediate Similarity	NPD7260	Phase 2
0.7172	Intermediate Similarity	NPD5362	Discontinued
0.7157	Intermediate Similarity	NPD6903	Approved
0.7157	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD6686	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7129	Intermediate Similarity	NPD4694	Approved
0.7129	Intermediate Similarity	NPD5280	Approved
0.7115	Intermediate Similarity	NPD6079	Approved
0.7105	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4786	Approved
0.7087	Intermediate Similarity	NPD5328	Approved
0.7087	Intermediate Similarity	NPD6904	Approved
0.7087	Intermediate Similarity	NPD6080	Approved
0.7087	Intermediate Similarity	NPD6673	Approved
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6319	Approved
0.7054	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5363	Approved
0.7027	Intermediate Similarity	NPD5141	Approved
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7019	Intermediate Similarity	NPD7838	Discovery
0.7018	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD6695	Phase 3
0.6972	Remote Similarity	NPD5286	Approved
0.6972	Remote Similarity	NPD4696	Approved
0.6972	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD5690	Phase 2
0.6952	Remote Similarity	NPD8034	Phase 2
0.6952	Remote Similarity	NPD5693	Phase 1
0.6952	Remote Similarity	NPD8035	Phase 2
0.6949	Remote Similarity	NPD6009	Approved
0.6944	Remote Similarity	NPD4755	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5654	Approved
0.6911	Remote Similarity	NPD7507	Approved
0.6909	Remote Similarity	NPD5223	Approved
0.6903	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD4221	Approved
0.69	Remote Similarity	NPD4223	Phase 3
0.69	Remote Similarity	NPD3667	Approved
0.6893	Remote Similarity	NPD7750	Discontinued
0.6891	Remote Similarity	NPD6335	Approved
0.6887	Remote Similarity	NPD4202	Approved
0.6885	Remote Similarity	NPD7604	Phase 2
0.6869	Remote Similarity	NPD4820	Approved
0.6869	Remote Similarity	NPD4819	Approved
0.6869	Remote Similarity	NPD4822	Approved
0.6869	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4821	Approved
0.6864	Remote Similarity	NPD6274	Approved
0.6863	Remote Similarity	NPD1694	Approved
0.6863	Remote Similarity	NPD5329	Approved
0.686	Remote Similarity	NPD7503	Approved
0.686	Remote Similarity	NPD5983	Phase 2
0.6852	Remote Similarity	NPD5222	Approved
0.6852	Remote Similarity	NPD5221	Approved
0.6852	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7839	Suspended
0.685	Remote Similarity	NPD6845	Suspended
0.6847	Remote Similarity	NPD4633	Approved
0.6847	Remote Similarity	NPD5226	Approved
0.6847	Remote Similarity	NPD7632	Discontinued
0.6847	Remote Similarity	NPD5224	Approved
0.6847	Remote Similarity	NPD5225	Approved
0.6833	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD7100	Approved
0.6832	Remote Similarity	NPD7154	Phase 3
0.6829	Remote Similarity	NPD7492	Approved
0.6827	Remote Similarity	NPD4518	Approved
0.6827	Remote Similarity	NPD5208	Approved
0.6822	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4700	Approved
0.6807	Remote Similarity	NPD6317	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD5786	Approved
0.6796	Remote Similarity	NPD3618	Phase 1
0.6796	Remote Similarity	NPD6098	Approved
0.6792	Remote Similarity	NPD7515	Phase 2
0.6789	Remote Similarity	NPD5173	Approved
0.6789	Remote Similarity	NPD5959	Approved
0.6786	Remote Similarity	NPD5174	Approved
0.6786	Remote Similarity	NPD5175	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD6336	Discontinued
0.6765	Remote Similarity	NPD4197	Approved
0.6762	Remote Similarity	NPD6051	Approved
0.6759	Remote Similarity	NPD5210	Approved
0.6759	Remote Similarity	NPD4629	Approved
0.6759	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD6314	Approved
0.6746	Remote Similarity	NPD7319	Approved
0.6733	Remote Similarity	NPD4270	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6733	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD7524	Approved
0.6731	Remote Similarity	NPD4250	Approved
0.6731	Remote Similarity	NPD4251	Approved
0.6727	Remote Similarity	NPD4225	Approved
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6868	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD7078	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.6701	Remote Similarity	NPD8039	Approved
0.67	Remote Similarity	NPD6931	Approved
0.67	Remote Similarity	NPD6930	Phase 2
0.6699	Remote Similarity	NPD1696	Phase 3
0.6698	Remote Similarity	NPD4096	Approved
0.6697	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6639	Remote Similarity	NPD6059	Approved

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