NPASS Compound

Structure

NPC217559 OpenBabel07101718242D 34 38 0 0 1 0 0 0 0 0999 V2000 2.4034 -0.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5352 0.2668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2744 2.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7803 1.5618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3996 -0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2744 -1.8485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9186 0.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5868 1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4306 1.5618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2590 -1.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9621 0.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9621 3.0233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0825 -1.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 2.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2280 -1.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 -0.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8586 -1.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2931 0.7179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5868 0.1002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8627 -0.5518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9621 1.0746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2744 1.0746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8059 2.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6132 -0.7572 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5862 -0.7062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 1.5618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8059 1.5618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4306 -0.3870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2744 0.1002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9096 -0.3492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2674 0.7179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6497 3.0233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 -1.5234 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 25 1 0 0 0 0 2 25 1 0 0 0 0 5 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 27 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 10 1 1 0 0 0 20 30 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 25 1 6 0 0 0 24 34 1 0 0 0 0 25 33 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 6 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	4.566
LogD:	4.365
LogS:	-4.46
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	4.946
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.017
MDCK Permeability:	1.857992356235627e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	89.42655944824219%
Volume Distribution (VD):	1.02
Pgp-substrate:	2.211318254470825%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	5.614
Half-life (T1/2):	0.388

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.911
Carcinogencity:	0.04
Eye Corrosion:	0.279
Eye Irritation:	0.168
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC217559

Natural Product ID:	NPC217559
*Common Name:**	(4S,20S,24S)-Epoxy-25,29-Dihydroxydammar-3-One
IUPAC Name:	(4S,5R,8R,9R,10R,13R,14R,17S)-4-(hydroxymethyl)-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,8,10,14-tetramethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	YQRDVNAQIGPOEY-BKOUEHDESA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-25(2,33)24-13-17-30(7,34-24)20-10-15-28(5)19(20)8-9-22-26(3)14-12-23(32)27(4,18-31)21(26)11-16-29(22,28)6/h19-22,24,31,33H,8-18H2,1-7H3/t19-,20+,21-,22-,24+,26+,27-,28-,29-,30+/m1/s1
SMILES:	OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]2[C@]1(C)CC[C@H](O1)C(O)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109466
PubChem CID:	76335697
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
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[481021]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[481021]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[481021]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[481021]

☑ 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 NPC217559 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	355
0.1-0.2	3080
0.2-0.3	10325
0.3-0.4	13124
0.4-0.5	6015
0.5-0.6	6028
0.6-0.7	3059
0.7-0.8	625
0.8-0.85	67
0.85-0.9	12
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292458
1.0	High Similarity	NPC268578
0.9481	High Similarity	NPC245029
0.9481	High Similarity	NPC31302
0.9146	High Similarity	NPC80700
0.9146	High Similarity	NPC474448
0.8889	High Similarity	NPC164289
0.8889	High Similarity	NPC242771
0.8889	High Similarity	NPC100366
0.8889	High Similarity	NPC311642
0.869	High Similarity	NPC92139
0.869	High Similarity	NPC472745
0.8659	High Similarity	NPC148740
0.8659	High Similarity	NPC102156
0.8605	High Similarity	NPC61688
0.8588	High Similarity	NPC474174
0.8588	High Similarity	NPC251808
0.8554	High Similarity	NPC472744
0.85	High Similarity	NPC264602
0.8452	Intermediate Similarity	NPC471044
0.8452	Intermediate Similarity	NPC473336
0.8444	Intermediate Similarity	NPC116683
0.8434	Intermediate Similarity	NPC477935
0.8434	Intermediate Similarity	NPC477936
0.8427	Intermediate Similarity	NPC206878
0.8415	Intermediate Similarity	NPC470609
0.8415	Intermediate Similarity	NPC472853
0.8372	Intermediate Similarity	NPC263802
0.8372	Intermediate Similarity	NPC202937
0.8354	Intermediate Similarity	NPC472854
0.8313	Intermediate Similarity	NPC77311
0.8272	Intermediate Similarity	NPC474574
0.8272	Intermediate Similarity	NPC133596
0.8272	Intermediate Similarity	NPC11907
0.8272	Intermediate Similarity	NPC477918
0.8272	Intermediate Similarity	NPC64081
0.8256	Intermediate Similarity	NPC114378
0.8256	Intermediate Similarity	NPC103782
0.825	Intermediate Similarity	NPC270306
0.825	Intermediate Similarity	NPC91387
0.825	Intermediate Similarity	NPC231680
0.8235	Intermediate Similarity	NPC50438
0.8171	Intermediate Similarity	NPC476732
0.8171	Intermediate Similarity	NPC199965
0.8148	Intermediate Similarity	NPC477932
0.8148	Intermediate Similarity	NPC477933
0.8118	Intermediate Similarity	NPC111582
0.8118	Intermediate Similarity	NPC477285
0.8118	Intermediate Similarity	NPC259173
0.8101	Intermediate Similarity	NPC58057
0.8101	Intermediate Similarity	NPC151018
0.8101	Intermediate Similarity	NPC473267
0.8101	Intermediate Similarity	NPC320549
0.8101	Intermediate Similarity	NPC156277
0.8095	Intermediate Similarity	NPC58631
0.8095	Intermediate Similarity	NPC190940
0.8085	Intermediate Similarity	NPC178853
0.8072	Intermediate Similarity	NPC80891
0.8072	Intermediate Similarity	NPC81074
0.8072	Intermediate Similarity	NPC201276
0.8072	Intermediate Similarity	NPC477282
0.8068	Intermediate Similarity	NPC229407
0.8068	Intermediate Similarity	NPC250687
0.8068	Intermediate Similarity	NPC56777
0.8068	Intermediate Similarity	NPC201607
0.8068	Intermediate Similarity	NPC48824
0.8068	Intermediate Similarity	NPC254572
0.8049	Intermediate Similarity	NPC477919
0.8049	Intermediate Similarity	NPC180199
0.8046	Intermediate Similarity	NPC476727
0.8046	Intermediate Similarity	NPC476726
0.8043	Intermediate Similarity	NPC476728
0.8025	Intermediate Similarity	NPC27349
0.8025	Intermediate Similarity	NPC477934
0.8025	Intermediate Similarity	NPC24014
0.8023	Intermediate Similarity	NPC474996
0.8022	Intermediate Similarity	NPC470423
0.8	Intermediate Similarity	NPC471747
0.8	Intermediate Similarity	NPC121121
0.8	Intermediate Similarity	NPC317066
0.8	Intermediate Similarity	NPC286719
0.8	Intermediate Similarity	NPC310766
0.8	Intermediate Similarity	NPC477286
0.8	Intermediate Similarity	NPC232112
0.7978	Intermediate Similarity	NPC269267
0.7978	Intermediate Similarity	NPC200580
0.7978	Intermediate Similarity	NPC24705
0.7978	Intermediate Similarity	NPC56962
0.7975	Intermediate Similarity	NPC476731
0.7952	Intermediate Similarity	NPC171426
0.7952	Intermediate Similarity	NPC324700
0.7952	Intermediate Similarity	NPC34046
0.7952	Intermediate Similarity	NPC224802
0.7952	Intermediate Similarity	NPC80089
0.7935	Intermediate Similarity	NPC17336
0.7907	Intermediate Similarity	NPC269684
0.7901	Intermediate Similarity	NPC254340
0.7901	Intermediate Similarity	NPC477930
0.7882	Intermediate Similarity	NPC50658
0.7882	Intermediate Similarity	NPC469745
0.7882	Intermediate Similarity	NPC12933
0.7875	Intermediate Similarity	NPC469940
0.7865	Intermediate Similarity	NPC226491
0.7865	Intermediate Similarity	NPC477614
0.7865	Intermediate Similarity	NPC471221
0.7857	Intermediate Similarity	NPC52951
0.7848	Intermediate Similarity	NPC213178
0.7848	Intermediate Similarity	NPC327728
0.7848	Intermediate Similarity	NPC131892
0.7848	Intermediate Similarity	NPC321732
0.7848	Intermediate Similarity	NPC6120
0.7848	Intermediate Similarity	NPC324607
0.7841	Intermediate Similarity	NPC215968
0.7841	Intermediate Similarity	NPC472272
0.7841	Intermediate Similarity	NPC155531
0.7831	Intermediate Similarity	NPC475031
0.7831	Intermediate Similarity	NPC23884
0.7826	Intermediate Similarity	NPC470424
0.7816	Intermediate Similarity	NPC34984
0.7816	Intermediate Similarity	NPC25037
0.7816	Intermediate Similarity	NPC319909
0.7816	Intermediate Similarity	NPC477434
0.7805	Intermediate Similarity	NPC21220
0.7805	Intermediate Similarity	NPC97534
0.7805	Intermediate Similarity	NPC159789
0.7805	Intermediate Similarity	NPC195155
0.7805	Intermediate Similarity	NPC273366
0.7805	Intermediate Similarity	NPC174964
0.7805	Intermediate Similarity	NPC125767
0.7791	Intermediate Similarity	NPC268040
0.7791	Intermediate Similarity	NPC61107
0.7791	Intermediate Similarity	NPC289486
0.7791	Intermediate Similarity	NPC475388
0.7791	Intermediate Similarity	NPC13494
0.7778	Intermediate Similarity	NPC474123
0.7766	Intermediate Similarity	NPC253586
0.775	Intermediate Similarity	NPC477929
0.7742	Intermediate Similarity	NPC215570
0.7738	Intermediate Similarity	NPC185465
0.7722	Intermediate Similarity	NPC473225
0.7717	Intermediate Similarity	NPC161035
0.7717	Intermediate Similarity	NPC476189
0.7711	Intermediate Similarity	NPC472487
0.7711	Intermediate Similarity	NPC472486
0.7711	Intermediate Similarity	NPC475742
0.7711	Intermediate Similarity	NPC5767
0.7711	Intermediate Similarity	NPC4209
0.7701	Intermediate Similarity	NPC470070
0.7692	Intermediate Similarity	NPC185529
0.7692	Intermediate Similarity	NPC472146
0.7692	Intermediate Similarity	NPC475056
0.7683	Intermediate Similarity	NPC472944
0.7683	Intermediate Similarity	NPC280026
0.7683	Intermediate Similarity	NPC167702
0.7683	Intermediate Similarity	NPC472945
0.7667	Intermediate Similarity	NPC255176
0.7667	Intermediate Similarity	NPC476435
0.7654	Intermediate Similarity	NPC197701
0.7654	Intermediate Similarity	NPC131506
0.7654	Intermediate Similarity	NPC89310
0.7654	Intermediate Similarity	NPC157777
0.7647	Intermediate Similarity	NPC320144
0.764	Intermediate Similarity	NPC302111
0.764	Intermediate Similarity	NPC477283
0.7625	Intermediate Similarity	NPC319671
0.7625	Intermediate Similarity	NPC476734
0.7625	Intermediate Similarity	NPC252032
0.7625	Intermediate Similarity	NPC469941
0.7619	Intermediate Similarity	NPC474404
0.7619	Intermediate Similarity	NPC317913
0.7619	Intermediate Similarity	NPC221420
0.7619	Intermediate Similarity	NPC171658
0.7619	Intermediate Similarity	NPC207010
0.7614	Intermediate Similarity	NPC237938
0.7614	Intermediate Similarity	NPC219535
0.7604	Intermediate Similarity	NPC108371
0.76	Intermediate Similarity	NPC224414
0.759	Intermediate Similarity	NPC472311
0.759	Intermediate Similarity	NPC212733
0.7586	Intermediate Similarity	NPC328007
0.7586	Intermediate Similarity	NPC202688
0.7586	Intermediate Similarity	NPC60018
0.7586	Intermediate Similarity	NPC154043
0.7586	Intermediate Similarity	NPC24556
0.7582	Intermediate Similarity	NPC471459
0.7582	Intermediate Similarity	NPC67653
0.7579	Intermediate Similarity	NPC170978
0.7576	Intermediate Similarity	NPC472655
0.7561	Intermediate Similarity	NPC153719
0.7561	Intermediate Similarity	NPC81759
0.7558	Intermediate Similarity	NPC1882
0.7558	Intermediate Similarity	NPC261616
0.7556	Intermediate Similarity	NPC239938
0.7556	Intermediate Similarity	NPC469322
0.7553	Intermediate Similarity	NPC305808
0.7553	Intermediate Similarity	NPC62407
0.7553	Intermediate Similarity	NPC287354
0.7549	Intermediate Similarity	NPC473062
0.7529	Intermediate Similarity	NPC471045
0.7528	Intermediate Similarity	NPC131350

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 NPC217559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	3391
0.2-0.3	3697
0.3-0.4	1002
0.4-0.5	276
0.5-0.6	271
0.6-0.7	97
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8101	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4244	Approved
0.7975	Intermediate Similarity	NPD4245	Approved
0.7975	Intermediate Similarity	NPD4789	Approved
0.7952	Intermediate Similarity	NPD6118	Approved
0.7952	Intermediate Similarity	NPD6115	Approved
0.7952	Intermediate Similarity	NPD6114	Approved
0.7952	Intermediate Similarity	NPD6697	Approved
0.7848	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3698	Phase 2
0.7848	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD3703	Phase 2
0.7792	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5360	Phase 3
0.7711	Intermediate Similarity	NPD6117	Approved
0.7683	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6116	Phase 1
0.7475	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5777	Approved
0.7439	Intermediate Similarity	NPD6081	Approved
0.7407	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3702	Approved
0.725	Intermediate Similarity	NPD4224	Phase 2
0.7229	Intermediate Similarity	NPD4758	Discontinued
0.7126	Intermediate Similarity	NPD3671	Phase 1
0.7126	Intermediate Similarity	NPD5364	Discontinued
0.7111	Intermediate Similarity	NPD4788	Approved
0.6966	Remote Similarity	NPD6928	Phase 2
0.6848	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD8171	Discontinued
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4787	Phase 1
0.6701	Remote Similarity	NPD8035	Phase 2
0.6701	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD6054	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD1700	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.663	Remote Similarity	NPD3667	Approved
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6370	Approved
0.6556	Remote Similarity	NPD4238	Approved
0.6556	Remote Similarity	NPD4802	Phase 2
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD4753	Phase 2
0.6495	Remote Similarity	NPD5328	Approved
0.6491	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD6015	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3666	Approved
0.6481	Remote Similarity	NPD4634	Approved
0.6466	Remote Similarity	NPD7492	Approved
0.6455	Remote Similarity	NPD8133	Approved
0.6441	Remote Similarity	NPD7736	Approved
0.6435	Remote Similarity	NPD5988	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD6920	Discontinued
0.641	Remote Similarity	NPD6616	Approved
0.6408	Remote Similarity	NPD8418	Phase 2
0.6404	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6356	Remote Similarity	NPD7078	Approved
0.6356	Remote Similarity	NPD8293	Discontinued
0.6354	Remote Similarity	NPD3618	Phase 1
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6940	Discontinued
0.6311	Remote Similarity	NPD7638	Approved
0.6306	Remote Similarity	NPD4632	Approved
0.6303	Remote Similarity	NPD6033	Approved
0.63	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6289	Remote Similarity	NPD7524	Approved
0.6277	Remote Similarity	NPD4223	Phase 3
0.6277	Remote Similarity	NPD4221	Approved
0.6262	Remote Similarity	NPD5739	Approved
0.6262	Remote Similarity	NPD6402	Approved
0.6262	Remote Similarity	NPD7128	Approved
0.6262	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD7525	Registered
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6903	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6224	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD4755	Approved
0.6196	Remote Similarity	NPD3617	Approved
0.6186	Remote Similarity	NPD5279	Phase 3
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD5210	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6176	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4139	Approved
0.617	Remote Similarity	NPD4692	Approved
0.6168	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD6881	Approved
0.6147	Remote Similarity	NPD6899	Approved
0.6146	Remote Similarity	NPD3668	Phase 3
0.6146	Remote Similarity	NPD4197	Approved
0.6134	Remote Similarity	NPD7507	Approved
0.6132	Remote Similarity	NPD7632	Discontinued
0.6117	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4697	Phase 3
0.6117	Remote Similarity	NPD5222	Approved
0.6117	Remote Similarity	NPD5221	Approved
0.6111	Remote Similarity	NPD6008	Approved
0.6098	Remote Similarity	NPD3198	Approved
0.6095	Remote Similarity	NPD4700	Approved
0.6095	Remote Similarity	NPD4696	Approved
0.6095	Remote Similarity	NPD5285	Approved
0.6095	Remote Similarity	NPD5286	Approved
0.6091	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6372	Approved
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7748	Approved
0.6066	Remote Similarity	NPD5956	Approved
0.6058	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD5697	Approved
0.6055	Remote Similarity	NPD5701	Approved
0.6042	Remote Similarity	NPD6695	Phase 3
0.604	Remote Similarity	NPD7637	Suspended
0.604	Remote Similarity	NPD7515	Phase 2
0.6038	Remote Similarity	NPD5223	Approved
0.6036	Remote Similarity	NPD7102	Approved
0.6036	Remote Similarity	NPD6883	Approved
0.6036	Remote Similarity	NPD7290	Approved
0.6034	Remote Similarity	NPD4522	Approved
0.602	Remote Similarity	NPD4690	Approved
0.602	Remote Similarity	NPD4689	Approved
0.602	Remote Similarity	NPD6098	Approved
0.602	Remote Similarity	NPD4693	Phase 3
0.602	Remote Similarity	NPD5205	Approved
0.602	Remote Similarity	NPD4688	Approved
0.602	Remote Similarity	NPD4138	Approved
0.6019	Remote Similarity	NPD7991	Discontinued
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD6415	Discontinued
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD371	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6650	Approved
0.5982	Remote Similarity	NPD6649	Approved
0.5982	Remote Similarity	NPD8130	Phase 1
0.5982	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6847	Approved
0.5982	Remote Similarity	NPD6869	Approved
0.5981	Remote Similarity	NPD4633	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD5224	Approved
0.5981	Remote Similarity	NPD5225	Approved
0.5981	Remote Similarity	NPD5226	Approved
0.5979	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6933	Approved
0.5966	Remote Similarity	NPD7604	Phase 2
0.5966	Remote Similarity	NPD6067	Discontinued
0.5946	Remote Similarity	NPD6012	Approved
0.5946	Remote Similarity	NPD6013	Approved
0.5946	Remote Similarity	NPD6014	Approved
0.5932	Remote Similarity	NPD6921	Approved
0.5932	Remote Similarity	NPD5983	Phase 2
0.5929	Remote Similarity	NPD6882	Approved
0.5926	Remote Similarity	NPD5174	Approved
0.5926	Remote Similarity	NPD5175	Approved
0.5926	Remote Similarity	NPD4754	Approved
0.5922	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD6705	Phase 1
0.5905	Remote Similarity	NPD7902	Approved
0.5876	Remote Similarity	NPD3669	Approved
0.5876	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5141	Approved
0.587	Remote Similarity	NPD7339	Approved
0.587	Remote Similarity	NPD6942	Approved
0.5868	Remote Similarity	NPD6336	Discontinued
0.5859	Remote Similarity	NPD5280	Approved
0.5859	Remote Similarity	NPD4694	Approved
0.5859	Remote Similarity	NPD5690	Phase 2

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