NPASS Compound

Structure

CID155531 OpenBabel06191715522D 41 45 0 0 1 0 0 0 0 0999 V2000 4.9784 -4.7903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 -4.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1799 -1.4197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1800 -2.4127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5319 -1.6467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9294 -0.9027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.5072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 0.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8700 0.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7999 -2.4134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6589 0.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4900 -0.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8895 -1.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8295 1.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6600 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1455 -1.3722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4895 -3.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1489 -4.3112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8302 -4.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6595 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8294 -1.4373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4900 -1.4376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8300 -1.4376 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6925 -1.4533 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3195 -2.8742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6598 -2.8747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8295 -0.4789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3198 -1.9163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5863 -1.7965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4886 -0.4784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6601 -1.9168 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3193 -4.7901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0007 -4.7906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6801 -1.9285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7361 -2.7421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1490 -3.3533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8302 -3.3537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4447 -0.5286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 32 1 0 0 0 0 15 31 1 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 18 27 1 0 0 0 0 19 35 2 0 0 0 0 19 39 1 0 0 0 0 20 36 2 0 0 0 0 20 40 1 0 0 0 0 21 11 1 1 0 0 0 21 28 1 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 22 37 1 1 0 0 0 23 29 1 0 0 0 0 23 34 1 1 0 0 0 24 31 1 1 0 0 0 24 34 1 0 0 0 0 25 30 1 6 0 0 0 25 41 1 0 0 0 0 26 29 1 0 0 0 0 26 39 1 6 0 0 0 27 34 1 1 0 0 0 27 40 1 0 0 0 0 28 32 1 6 0 0 0 30 38 1 0 0 0 0 31 32 1 6 0 0 0 32 8 1 6 0 0 0 33 9 1 1 0 0 0 33 41 1 0 0 0 0 34 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.4
Volume:	610.096
LogP:	4.91
LogD:	4.453
LogS:	-4.692
# Rotatable Bonds:	6
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.267
Fsp3:	0.941
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:	-4.837
MDCK Permeability:	3.543969432939775e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	79.48624420166016%
Volume Distribution (VD):	1.051
Pgp-substrate:	13.085359573364258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	3.546
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.443
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.733
Skin Sensitization:	0.925
Carcinogencity:	0.024
Eye Corrosion:	0.692
Eye Irritation:	0.1
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC155531

Natural Product ID:	NPC155531
*Common Name:**	Rel-1Beta,3Alpha-Diacetoxy-12Beta,25-Dihydroxy-(20S,24R)-Epoxydammarane
IUPAC Name:	[(1R,3R,5S,8R,9S,10R,12R,13R,14R,17S)-1-acetyloxy-12-hydroxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	WSLDSLPNFRQNCB-AYJXGDQBSA-N
Standard InCHI:	InChI=1S/C34H56O7/c1-19(35)39-26-18-27(40-20(2)36)34(10)23(29(26,3)4)12-15-31(7)24(34)17-22(37)28-21(11-14-32(28,31)8)33(9)16-13-25(41-33)30(5,6)38/h21-28,37-38H,11-18H2,1-10H3/t21-,22+,23-,24-,25+,26+,27+,28-,31+,32+,33-,34-/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](OC(=O)C)C([C@H]2[C@@]1(C)[C@H]1C[C@@H](O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]3[C@]1(C)CC[C@@H](O1)C(O)(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455074
PubChem CID:	11444566
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	El Volcan, Dpto. La Capital, Province of San Luis, Argentina	2001-MAR	PMID[14695802]
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15834	Bonellia viridis	Species	Bonelliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22484	Aplidium cyaneum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23888	Chrysothamnus viscidiflorus	Species	Asteraceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[520121]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[520121]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[520121]

☑ 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 NPC155531 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	406
0.1-0.2	3468
0.2-0.3	10582
0.3-0.4	12981
0.4-0.5	5529
0.5-0.6	4993
0.6-0.7	3500
0.7-0.8	1074
0.8-0.85	112
0.85-0.9	31
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215968
0.9753	High Similarity	NPC477283
0.9625	High Similarity	NPC477285
0.9625	High Similarity	NPC111582
0.95	High Similarity	NPC286719
0.95	High Similarity	NPC477286
0.9375	High Similarity	NPC190940
0.9259	High Similarity	NPC202688
0.9259	High Similarity	NPC154043
0.9259	High Similarity	NPC60018
0.9259	High Similarity	NPC477284
0.9186	High Similarity	NPC473066
0.9157	High Similarity	NPC266651
0.9125	High Similarity	NPC477282
0.9125	High Similarity	NPC81074
0.9125	High Similarity	NPC477287
0.9059	High Similarity	NPC201607
0.9059	High Similarity	NPC56777
0.9048	High Similarity	NPC114378
0.9048	High Similarity	NPC103782
0.8902	High Similarity	NPC73515
0.8875	High Similarity	NPC11907
0.8875	High Similarity	NPC133596
0.8875	High Similarity	NPC64081
0.8875	High Similarity	NPC474574
0.8864	High Similarity	NPC182740
0.8864	High Similarity	NPC211845
0.8864	High Similarity	NPC122083
0.8864	High Similarity	NPC256104
0.8795	High Similarity	NPC477447
0.8795	High Similarity	NPC470155
0.8795	High Similarity	NPC477446
0.878	High Similarity	NPC472951
0.878	High Similarity	NPC472943
0.8778	High Similarity	NPC116683
0.8778	High Similarity	NPC237071
0.8778	High Similarity	NPC238796
0.8778	High Similarity	NPC156377
0.8778	High Similarity	NPC203434
0.8721	High Similarity	NPC5943
0.8675	High Similarity	NPC470156
0.8675	High Similarity	NPC470154
0.8659	High Similarity	NPC220379
0.8659	High Similarity	NPC476176
0.8642	High Similarity	NPC212453
0.8625	High Similarity	NPC231680
0.8625	High Similarity	NPC91387
0.8625	High Similarity	NPC270306
0.8605	High Similarity	NPC131365
0.8602	High Similarity	NPC475574
0.8588	High Similarity	NPC320824
0.8588	High Similarity	NPC18953
0.8571	High Similarity	NPC475388
0.8556	High Similarity	NPC151214
0.8556	High Similarity	NPC191915
0.8554	High Similarity	NPC474714
0.8554	High Similarity	NPC16449
0.8539	High Similarity	NPC219516
0.8537	High Similarity	NPC471045
0.8523	High Similarity	NPC82955
0.8506	High Similarity	NPC62202
0.8506	High Similarity	NPC213658
0.8506	High Similarity	NPC45833
0.8506	High Similarity	NPC210658
0.8506	High Similarity	NPC110365
0.8506	High Similarity	NPC161928
0.85	High Similarity	NPC472944
0.85	High Similarity	NPC472945
0.8495	Intermediate Similarity	NPC470030
0.8471	Intermediate Similarity	NPC470070
0.8471	Intermediate Similarity	NPC69953
0.8462	Intermediate Similarity	NPC21897
0.8462	Intermediate Similarity	NPC57964
0.8462	Intermediate Similarity	NPC94582
0.8444	Intermediate Similarity	NPC167644
0.8444	Intermediate Similarity	NPC311246
0.8427	Intermediate Similarity	NPC470114
0.8415	Intermediate Similarity	NPC171658
0.8409	Intermediate Similarity	NPC128475
0.8404	Intermediate Similarity	NPC476512
0.8404	Intermediate Similarity	NPC472081
0.8404	Intermediate Similarity	NPC108227
0.8395	Intermediate Similarity	NPC158208
0.8395	Intermediate Similarity	NPC243027
0.8395	Intermediate Similarity	NPC196136
0.8391	Intermediate Similarity	NPC471411
0.8391	Intermediate Similarity	NPC471410
0.8387	Intermediate Similarity	NPC292775
0.837	Intermediate Similarity	NPC296936
0.837	Intermediate Similarity	NPC252056
0.8353	Intermediate Similarity	NPC311642
0.8353	Intermediate Similarity	NPC470611
0.8353	Intermediate Similarity	NPC100366
0.8353	Intermediate Similarity	NPC242771
0.8353	Intermediate Similarity	NPC164289
0.8352	Intermediate Similarity	NPC113500
0.8352	Intermediate Similarity	NPC477224
0.8352	Intermediate Similarity	NPC3538
0.8333	Intermediate Similarity	NPC210759
0.8333	Intermediate Similarity	NPC229801
0.8333	Intermediate Similarity	NPC307167
0.8316	Intermediate Similarity	NPC134967
0.8316	Intermediate Similarity	NPC310138
0.8316	Intermediate Similarity	NPC470029
0.8316	Intermediate Similarity	NPC114700
0.8315	Intermediate Similarity	NPC20822
0.8313	Intermediate Similarity	NPC43463
0.8295	Intermediate Similarity	NPC140446
0.8295	Intermediate Similarity	NPC43912
0.8293	Intermediate Similarity	NPC136424
0.8276	Intermediate Similarity	NPC290612
0.8272	Intermediate Similarity	NPC228994
0.8272	Intermediate Similarity	NPC192501
0.8272	Intermediate Similarity	NPC10476
0.8256	Intermediate Similarity	NPC29342
0.8256	Intermediate Similarity	NPC2572
0.825	Intermediate Similarity	NPC187471
0.825	Intermediate Similarity	NPC252182
0.825	Intermediate Similarity	NPC470071
0.825	Intermediate Similarity	NPC1340
0.8229	Intermediate Similarity	NPC139181
0.8229	Intermediate Similarity	NPC476837
0.8229	Intermediate Similarity	NPC97260
0.8222	Intermediate Similarity	NPC473542
0.8222	Intermediate Similarity	NPC279329
0.8222	Intermediate Similarity	NPC10274
0.8202	Intermediate Similarity	NPC473436
0.8202	Intermediate Similarity	NPC476435
0.8202	Intermediate Similarity	NPC476379
0.8193	Intermediate Similarity	NPC128951
0.8193	Intermediate Similarity	NPC185915
0.8193	Intermediate Similarity	NPC477227
0.8193	Intermediate Similarity	NPC105208
0.8193	Intermediate Similarity	NPC192046
0.8193	Intermediate Similarity	NPC302578
0.8182	Intermediate Similarity	NPC80700
0.8171	Intermediate Similarity	NPC472952
0.8171	Intermediate Similarity	NPC317242
0.8171	Intermediate Similarity	NPC472950
0.8171	Intermediate Similarity	NPC186851
0.8152	Intermediate Similarity	NPC473774
0.8152	Intermediate Similarity	NPC175
0.8152	Intermediate Similarity	NPC252253
0.8152	Intermediate Similarity	NPC45959
0.8152	Intermediate Similarity	NPC24960
0.8152	Intermediate Similarity	NPC305418
0.814	Intermediate Similarity	NPC121121
0.814	Intermediate Similarity	NPC2096
0.814	Intermediate Similarity	NPC208912
0.8132	Intermediate Similarity	NPC5632
0.8132	Intermediate Similarity	NPC149966
0.8132	Intermediate Similarity	NPC36372
0.8132	Intermediate Similarity	NPC293609
0.8111	Intermediate Similarity	NPC131466
0.8111	Intermediate Similarity	NPC228059
0.8095	Intermediate Similarity	NPC147993
0.8095	Intermediate Similarity	NPC191345
0.8095	Intermediate Similarity	NPC18857
0.8095	Intermediate Similarity	NPC67657
0.8095	Intermediate Similarity	NPC252483
0.8095	Intermediate Similarity	NPC471769
0.8085	Intermediate Similarity	NPC470591
0.8085	Intermediate Similarity	NPC477223
0.8085	Intermediate Similarity	NPC477222
0.8072	Intermediate Similarity	NPC163597
0.8068	Intermediate Similarity	NPC273290
0.8068	Intermediate Similarity	NPC232044
0.8065	Intermediate Similarity	NPC473065
0.8065	Intermediate Similarity	NPC473064
0.8065	Intermediate Similarity	NPC473067
0.8049	Intermediate Similarity	NPC304499
0.8049	Intermediate Similarity	NPC470151
0.8046	Intermediate Similarity	NPC474346
0.8046	Intermediate Similarity	NPC474253
0.8046	Intermediate Similarity	NPC475820
0.8046	Intermediate Similarity	NPC474284
0.8046	Intermediate Similarity	NPC213737
0.8043	Intermediate Similarity	NPC475307
0.8043	Intermediate Similarity	NPC88962
0.8043	Intermediate Similarity	NPC277774
0.8043	Intermediate Similarity	NPC144790
0.8043	Intermediate Similarity	NPC149400
0.8025	Intermediate Similarity	NPC157777
0.8025	Intermediate Similarity	NPC131506
0.8023	Intermediate Similarity	NPC211049
0.8023	Intermediate Similarity	NPC116320
0.8023	Intermediate Similarity	NPC58631
0.8023	Intermediate Similarity	NPC119922
0.8022	Intermediate Similarity	NPC473269
0.8021	Intermediate Similarity	NPC476839
0.8021	Intermediate Similarity	NPC476838
0.8	Intermediate Similarity	NPC470067
0.8	Intermediate Similarity	NPC300179
0.8	Intermediate Similarity	NPC80891
0.8	Intermediate Similarity	NPC470068
0.8	Intermediate Similarity	NPC102426
0.8	Intermediate Similarity	NPC470872
0.8	Intermediate Similarity	NPC107919
0.8	Intermediate Similarity	NPC473638
0.8	Intermediate Similarity	NPC287452

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 NPC155531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	3754
0.2-0.3	3410
0.3-0.4	910
0.4-0.5	308
0.5-0.6	237
0.6-0.7	105
0.7-0.8	14
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
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6118	Approved
0.7882	Intermediate Similarity	NPD6114	Approved
0.7882	Intermediate Similarity	NPD6115	Approved
0.7882	Intermediate Similarity	NPD6697	Approved
0.7849	Intermediate Similarity	NPD8171	Discontinued
0.7765	Intermediate Similarity	NPD6116	Phase 1
0.7701	Intermediate Similarity	NPD6928	Phase 2
0.7647	Intermediate Similarity	NPD6117	Approved
0.7426	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7327	Approved
0.7091	Intermediate Similarity	NPD7328	Approved
0.7054	Intermediate Similarity	NPD8296	Approved
0.7054	Intermediate Similarity	NPD8380	Approved
0.7054	Intermediate Similarity	NPD8335	Approved
0.7054	Intermediate Similarity	NPD8379	Approved
0.7054	Intermediate Similarity	NPD8378	Approved
0.7027	Intermediate Similarity	NPD7516	Approved
0.701	Intermediate Similarity	NPD8035	Phase 2
0.701	Intermediate Similarity	NPD8034	Phase 2
0.6977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6961	Remote Similarity	NPD1700	Approved
0.6951	Remote Similarity	NPD371	Approved
0.6932	Remote Similarity	NPD3703	Phase 2
0.6903	Remote Similarity	NPD8033	Approved
0.6881	Remote Similarity	NPD8133	Approved
0.686	Remote Similarity	NPD4787	Phase 1
0.686	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7991	Discontinued
0.6765	Remote Similarity	NPD7638	Approved
0.6744	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3702	Approved
0.6739	Remote Similarity	NPD7525	Registered
0.6737	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5360	Phase 3
0.6628	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6940	Discontinued
0.6591	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD5777	Approved
0.6571	Remote Similarity	NPD7632	Discontinued
0.6555	Remote Similarity	NPD7736	Approved
0.6538	Remote Similarity	NPD8418	Phase 2
0.6526	Remote Similarity	NPD3669	Approved
0.6526	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7507	Approved
0.6514	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7319	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6477	Remote Similarity	NPD4789	Approved
0.6477	Remote Similarity	NPD4245	Approved
0.6477	Remote Similarity	NPD4244	Approved
0.6471	Remote Similarity	NPD8293	Discontinued
0.6444	Remote Similarity	NPD1811	Approved
0.6444	Remote Similarity	NPD1810	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD7524	Approved
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD7320	Approved
0.6395	Remote Similarity	NPD4224	Phase 2
0.6389	Remote Similarity	NPD5739	Approved
0.6389	Remote Similarity	NPD6402	Approved
0.6389	Remote Similarity	NPD6675	Approved
0.6389	Remote Similarity	NPD7128	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD3698	Phase 2
0.6333	Remote Similarity	NPD7078	Approved
0.6325	Remote Similarity	NPD7503	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6399	Phase 3
0.6273	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD6881	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6261	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6008	Approved
0.6222	Remote Similarity	NPD4758	Discontinued
0.6216	Remote Similarity	NPD6372	Approved
0.6216	Remote Similarity	NPD6373	Approved
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD6695	Phase 3
0.6186	Remote Similarity	NPD6016	Approved
0.6182	Remote Similarity	NPD6412	Phase 2
0.6182	Remote Similarity	NPD5697	Approved
0.6182	Remote Similarity	NPD5701	Approved
0.617	Remote Similarity	NPD3671	Phase 1
0.617	Remote Similarity	NPD5364	Discontinued
0.6162	Remote Similarity	NPD8308	Discontinued
0.6161	Remote Similarity	NPD7290	Approved
0.6161	Remote Similarity	NPD7102	Approved
0.6161	Remote Similarity	NPD6883	Approved
0.6134	Remote Similarity	NPD5988	Approved
0.6132	Remote Similarity	NPD4225	Approved
0.6126	Remote Similarity	NPD8174	Phase 2
0.6121	Remote Similarity	NPD7115	Discovery
0.6121	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD2686	Approved
0.6111	Remote Similarity	NPD2687	Approved
0.6111	Remote Similarity	NPD2254	Approved
0.6106	Remote Similarity	NPD6617	Approved
0.6106	Remote Similarity	NPD6649	Approved
0.6106	Remote Similarity	NPD6869	Approved
0.6106	Remote Similarity	NPD6847	Approved
0.6106	Remote Similarity	NPD6650	Approved
0.61	Remote Similarity	NPD7750	Discontinued
0.6083	Remote Similarity	NPD7604	Phase 2
0.6078	Remote Similarity	NPD6700	Approved
0.6078	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6013	Approved
0.6071	Remote Similarity	NPD6014	Approved
0.6071	Remote Similarity	NPD6012	Approved
0.6058	Remote Similarity	NPD7748	Approved
0.6053	Remote Similarity	NPD6882	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.605	Remote Similarity	NPD6921	Approved
0.6038	Remote Similarity	NPD7902	Approved
0.6038	Remote Similarity	NPD6084	Phase 2
0.6038	Remote Similarity	NPD6083	Phase 2
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD6702	Approved
0.6019	Remote Similarity	NPD5344	Discontinued
0.6019	Remote Similarity	NPD6703	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5982	Remote Similarity	NPD6011	Approved
0.5982	Remote Similarity	NPD6686	Approved
0.5979	Remote Similarity	NPD1780	Approved
0.5979	Remote Similarity	NPD1779	Approved
0.5965	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8328	Phase 3
0.5938	Remote Similarity	NPD7645	Phase 2
0.5888	Remote Similarity	NPD4755	Approved
0.5887	Remote Similarity	NPD6033	Approved
0.5877	Remote Similarity	NPD4634	Approved
0.5876	Remote Similarity	NPD6931	Approved
0.5876	Remote Similarity	NPD6930	Phase 2
0.5872	Remote Similarity	NPD4159	Approved
0.5865	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD4788	Approved
0.5856	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6942	Approved
0.5851	Remote Similarity	NPD7339	Approved
0.5849	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5328	Approved
0.5825	Remote Similarity	NPD6051	Approved
0.582	Remote Similarity	NPD6067	Discontinued
0.581	Remote Similarity	NPD4202	Approved
0.58	Remote Similarity	NPD4786	Approved
0.5789	Remote Similarity	NPD6933	Approved
0.578	Remote Similarity	NPD5286	Approved
0.578	Remote Similarity	NPD4696	Approved
0.578	Remote Similarity	NPD5285	Approved
0.578	Remote Similarity	NPD4700	Approved
0.5773	Remote Similarity	NPD6929	Approved
0.5763	Remote Similarity	NPD6274	Approved
0.5763	Remote Similarity	NPD7754	Approved
0.5763	Remote Similarity	NPD7755	Approved
0.5755	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7900	Approved
0.5752	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7101	Approved
0.575	Remote Similarity	NPD7100	Approved
0.5729	Remote Similarity	NPD6932	Approved
0.5726	Remote Similarity	NPD8298	Phase 2
0.5714	Remote Similarity	NPD4748	Discontinued
0.5714	Remote Similarity	NPD6079	Approved
0.5714	Remote Similarity	NPD6705	Phase 1
0.5714	Remote Similarity	NPD7087	Discontinued
0.5701	Remote Similarity	NPD5695	Phase 3
0.5688	Remote Similarity	NPD5696	Approved
0.5686	Remote Similarity	NPD3618	Phase 1
0.5676	Remote Similarity	NPD5211	Phase 2
0.5676	Remote Similarity	NPD5225	Approved
0.5676	Remote Similarity	NPD5224	Approved
0.5676	Remote Similarity	NPD4633	Approved
0.5676	Remote Similarity	NPD5226	Approved
0.5667	Remote Similarity	NPD6335	Approved
0.5664	Remote Similarity	NPD6920	Discontinued
0.5656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6908	Approved
0.5656	Remote Similarity	NPD6909	Approved
0.5641	Remote Similarity	NPD6053	Discontinued
0.5636	Remote Similarity	NPD6648	Approved
0.5631	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5175	Approved
0.5625	Remote Similarity	NPD3701	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