NPASS Compound

Structure

NPC80700 OpenBabel07101719512D 34 38 0 0 1 0 0 0 0 0999 V2000 -7.7803 1.5618 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 2.4034 -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 -4.3996 -0.4888 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 -4.2744 -1.8485 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 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 -0.8586 -1.3222 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 -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 -4.2744 1.0746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9621 1.0746 0.0000 C 0 0 1 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 -5.1183 -0.3870 0.0000 C 0 0 1 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 -6.8059 1.5618 0.0000 C 0 0 0 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 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 -0.9096 -0.3492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2744 0.1002 0.0000 C 0 0 2 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 -5.1183 -1.3613 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 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 11 1 1 0 0 0 19 29 1 0 0 0 0 20 27 1 1 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 1 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 26 1 6 0 0 0 24 34 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 1 0 0 0 28 30 1 1 0 0 0 29 7 1 6 0 0 0 29 34 1 0 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	4.732
LogD:	4.566
LogS:	-4.681
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	5.02
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:	-4.915
MDCK Permeability:	2.3292295736609958e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.319
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	89.27716064453125%
Volume Distribution (VD):	0.999
Pgp-substrate:	4.742697238922119%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	5.888
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.822
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.887
Carcinogencity:	0.053
Eye Corrosion:	0.285
Eye Irritation:	0.122
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC80700

Natural Product ID:	NPC80700
*Common Name:**	(20S,24S)-Epoxy-7Beta,25-Dihydroxydammar-3-One
IUPAC Name:	(5R,7S,8R,9R,10R,13R,14R,17S)-7-hydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	ACDWZMKZBRXXNE-MFWNHGFHSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-25(2)21-17-23(32)30(8)20(27(21,5)14-12-22(25)31)10-9-18-19(11-15-28(18,30)6)29(7)16-13-24(34-29)26(3,4)33/h18-21,23-24,32-33H,9-17H2,1-8H3/t18-,19+,20-,21+,23+,24+,27-,28-,29+,30+/m1/s1
SMILES:	CC1(C)[C@@H]2C[C@@H]([C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@@H](C(C)(C)O)O3)[C@@]2(C)CCC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109467
PubChem CID:	76313963
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[503869]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[503869]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[503869]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[503869]

☑ 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 NPC80700 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	378
0.1-0.2	3063
0.2-0.3	9076
0.3-0.4	14312
0.4-0.5	5813
0.5-0.6	5343
0.6-0.7	3626
0.7-0.8	938
0.8-0.85	106
0.85-0.9	35
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC268578
0.9146	High Similarity	NPC217559
0.9146	High Similarity	NPC292458
0.9125	High Similarity	NPC31302
0.9125	High Similarity	NPC245029
0.8953	High Similarity	NPC61688
0.8824	High Similarity	NPC474448
0.8824	High Similarity	NPC476726
0.8824	High Similarity	NPC476727
0.8778	High Similarity	NPC476728
0.8721	High Similarity	NPC263802
0.8721	High Similarity	NPC202937
0.8642	High Similarity	NPC133596
0.8642	High Similarity	NPC64081
0.8642	High Similarity	NPC11907
0.8642	High Similarity	NPC474574
0.8625	High Similarity	NPC159789
0.8625	High Similarity	NPC231680
0.8625	High Similarity	NPC91387
0.8625	High Similarity	NPC270306
0.8605	High Similarity	NPC472272
0.8588	High Similarity	NPC50438
0.8571	High Similarity	NPC311642
0.8571	High Similarity	NPC164289
0.8571	High Similarity	NPC268040
0.8571	High Similarity	NPC317066
0.8571	High Similarity	NPC242771
0.8571	High Similarity	NPC100366
0.8556	High Similarity	NPC470424
0.8554	High Similarity	NPC470609
0.8519	High Similarity	NPC472486
0.8519	High Similarity	NPC472487
0.8471	Intermediate Similarity	NPC477285
0.8471	Intermediate Similarity	NPC111582
0.8452	Intermediate Similarity	NPC58631
0.8452	Intermediate Similarity	NPC190940
0.8434	Intermediate Similarity	NPC80891
0.8434	Intermediate Similarity	NPC81074
0.8434	Intermediate Similarity	NPC477282
0.8434	Intermediate Similarity	NPC320144
0.8434	Intermediate Similarity	NPC201276
0.8427	Intermediate Similarity	NPC185529
0.8427	Intermediate Similarity	NPC472146
0.8415	Intermediate Similarity	NPC221420
0.8409	Intermediate Similarity	NPC476435
0.8395	Intermediate Similarity	NPC125767
0.8395	Intermediate Similarity	NPC21220
0.8391	Intermediate Similarity	NPC92139
0.8391	Intermediate Similarity	NPC472745
0.8375	Intermediate Similarity	NPC232112
0.8372	Intermediate Similarity	NPC473336
0.8372	Intermediate Similarity	NPC474996
0.8372	Intermediate Similarity	NPC471044
0.837	Intermediate Similarity	NPC116683
0.8353	Intermediate Similarity	NPC286719
0.8353	Intermediate Similarity	NPC61107
0.8353	Intermediate Similarity	NPC102156
0.8353	Intermediate Similarity	NPC148740
0.8353	Intermediate Similarity	NPC121121
0.8353	Intermediate Similarity	NPC289486
0.8353	Intermediate Similarity	NPC477286
0.8315	Intermediate Similarity	NPC24705
0.8315	Intermediate Similarity	NPC56962
0.8313	Intermediate Similarity	NPC80089
0.8313	Intermediate Similarity	NPC224802
0.8313	Intermediate Similarity	NPC34046
0.8313	Intermediate Similarity	NPC185465
0.8313	Intermediate Similarity	NPC324700
0.8313	Intermediate Similarity	NPC171426
0.8295	Intermediate Similarity	NPC251808
0.8295	Intermediate Similarity	NPC474174
0.8293	Intermediate Similarity	NPC5767
0.8293	Intermediate Similarity	NPC475742
0.8261	Intermediate Similarity	NPC17336
0.8261	Intermediate Similarity	NPC305808
0.8256	Intermediate Similarity	NPC327451
0.8256	Intermediate Similarity	NPC269684
0.8256	Intermediate Similarity	NPC472744
0.825	Intermediate Similarity	NPC320549
0.825	Intermediate Similarity	NPC58057
0.825	Intermediate Similarity	NPC156277
0.825	Intermediate Similarity	NPC151018
0.8242	Intermediate Similarity	NPC161035
0.8235	Intermediate Similarity	NPC12933
0.8235	Intermediate Similarity	NPC469745
0.8211	Intermediate Similarity	NPC178853
0.8202	Intermediate Similarity	NPC226491
0.8202	Intermediate Similarity	NPC477614
0.8193	Intermediate Similarity	NPC475031
0.8193	Intermediate Similarity	NPC23884
0.8193	Intermediate Similarity	NPC264602
0.8182	Intermediate Similarity	NPC215968
0.8182	Intermediate Similarity	NPC103782
0.8182	Intermediate Similarity	NPC155531
0.8182	Intermediate Similarity	NPC114378
0.8171	Intermediate Similarity	NPC195155
0.8171	Intermediate Similarity	NPC174964
0.8171	Intermediate Similarity	NPC273366
0.8171	Intermediate Similarity	NPC97534
0.8161	Intermediate Similarity	NPC291310
0.8161	Intermediate Similarity	NPC477434
0.8152	Intermediate Similarity	NPC470423
0.8144	Intermediate Similarity	NPC100078
0.814	Intermediate Similarity	NPC475388
0.8132	Intermediate Similarity	NPC52756
0.8125	Intermediate Similarity	NPC244969
0.8125	Intermediate Similarity	NPC213528
0.8118	Intermediate Similarity	NPC477851
0.8118	Intermediate Similarity	NPC472853
0.8111	Intermediate Similarity	NPC200580
0.809	Intermediate Similarity	NPC239938
0.8085	Intermediate Similarity	NPC472273
0.8072	Intermediate Similarity	NPC4209
0.8065	Intermediate Similarity	NPC470031
0.8061	Intermediate Similarity	NPC166079
0.8049	Intermediate Similarity	NPC133922
0.8049	Intermediate Similarity	NPC472854
0.8049	Intermediate Similarity	NPC254340
0.8046	Intermediate Similarity	NPC470070
0.8043	Intermediate Similarity	NPC476189
0.8041	Intermediate Similarity	NPC34562
0.8041	Intermediate Similarity	NPC471005
0.8025	Intermediate Similarity	NPC157777
0.8025	Intermediate Similarity	NPC131506
0.8025	Intermediate Similarity	NPC89310
0.8023	Intermediate Similarity	NPC77311
0.8022	Intermediate Similarity	NPC475056
0.8022	Intermediate Similarity	NPC77756
0.8	Intermediate Similarity	NPC201607
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC56777
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC131892
0.7979	Intermediate Similarity	NPC475785
0.7979	Intermediate Similarity	NPC163685
0.7978	Intermediate Similarity	NPC477283
0.7978	Intermediate Similarity	NPC302111
0.7976	Intermediate Similarity	NPC317913
0.7976	Intermediate Similarity	NPC207010
0.7959	Intermediate Similarity	NPC471293
0.7957	Intermediate Similarity	NPC217567
0.7957	Intermediate Similarity	NPC329713
0.7957	Intermediate Similarity	NPC76136
0.7955	Intermediate Similarity	NPC105895
0.7955	Intermediate Similarity	NPC219535
0.7955	Intermediate Similarity	NPC237938
0.7952	Intermediate Similarity	NPC212733
0.7931	Intermediate Similarity	NPC30583
0.7931	Intermediate Similarity	NPC202688
0.7931	Intermediate Similarity	NPC154043
0.7931	Intermediate Similarity	NPC60018
0.7927	Intermediate Similarity	NPC81759
0.7927	Intermediate Similarity	NPC153719
0.7912	Intermediate Similarity	NPC471459
0.7912	Intermediate Similarity	NPC67653
0.7907	Intermediate Similarity	NPC261616
0.7895	Intermediate Similarity	NPC471241
0.7895	Intermediate Similarity	NPC170978
0.7889	Intermediate Similarity	NPC470920
0.7882	Intermediate Similarity	NPC476732
0.7882	Intermediate Similarity	NPC199965
0.7879	Intermediate Similarity	NPC306776
0.7879	Intermediate Similarity	NPC215408
0.7872	Intermediate Similarity	NPC82633
0.7872	Intermediate Similarity	NPC62407
0.7872	Intermediate Similarity	NPC287354
0.7865	Intermediate Similarity	NPC473350
0.7857	Intermediate Similarity	NPC471046
0.7843	Intermediate Similarity	NPC473062
0.7841	Intermediate Similarity	NPC259173
0.7841	Intermediate Similarity	NPC227170
0.7835	Intermediate Similarity	NPC477172
0.7831	Intermediate Similarity	NPC280026
0.7831	Intermediate Similarity	NPC167702
0.7826	Intermediate Similarity	NPC476296
0.7826	Intermediate Similarity	NPC50443
0.7826	Intermediate Similarity	NPC136801
0.7826	Intermediate Similarity	NPC18536
0.7826	Intermediate Similarity	NPC470114
0.7816	Intermediate Similarity	NPC476071
0.7816	Intermediate Similarity	NPC50658
0.7812	Intermediate Similarity	NPC472144
0.7805	Intermediate Similarity	NPC252182
0.7805	Intermediate Similarity	NPC1340
0.7805	Intermediate Similarity	NPC470071
0.7805	Intermediate Similarity	NPC187471
0.7802	Intermediate Similarity	NPC250687
0.7802	Intermediate Similarity	NPC471221
0.7802	Intermediate Similarity	NPC48824
0.7802	Intermediate Similarity	NPC229407
0.7802	Intermediate Similarity	NPC476379
0.7802	Intermediate Similarity	NPC254572
0.7791	Intermediate Similarity	NPC477287
0.7791	Intermediate Similarity	NPC220379
0.7789	Intermediate Similarity	NPC193785
0.7789	Intermediate Similarity	NPC475765
0.7789	Intermediate Similarity	NPC235109
0.7778	Intermediate Similarity	NPC83242
0.7778	Intermediate Similarity	NPC66407

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 NPC80700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	3463
0.2-0.3	3592
0.3-0.4	1045
0.4-0.5	251
0.5-0.6	212
0.6-0.7	149
0.7-0.8	21
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD3703	Phase 2
0.8313	Intermediate Similarity	NPD6118	Approved
0.8313	Intermediate Similarity	NPD6697	Approved
0.8313	Intermediate Similarity	NPD6114	Approved
0.8313	Intermediate Similarity	NPD6115	Approved
0.825	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6116	Phase 1
0.7959	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5360	Phase 3
0.7875	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4244	Approved
0.7683	Intermediate Similarity	NPD4245	Approved
0.7683	Intermediate Similarity	NPD4789	Approved
0.7561	Intermediate Similarity	NPD3698	Phase 2
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4758	Discontinued
0.7326	Intermediate Similarity	NPD3702	Approved
0.7273	Intermediate Similarity	NPD5364	Discontinued
0.7273	Intermediate Similarity	NPD3671	Phase 1
0.7176	Intermediate Similarity	NPD5777	Approved
0.7176	Intermediate Similarity	NPD6081	Approved
0.7158	Intermediate Similarity	NPD5328	Approved
0.7111	Intermediate Similarity	NPD6928	Phase 2
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8034	Phase 2
0.701	Intermediate Similarity	NPD8035	Phase 2
0.701	Intermediate Similarity	NPD6079	Approved
0.6988	Remote Similarity	NPD4224	Phase 2
0.6964	Remote Similarity	NPD6054	Approved
0.6964	Remote Similarity	NPD6059	Approved
0.6961	Remote Similarity	NPD1700	Approved
0.6939	Remote Similarity	NPD8171	Discontinued
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7320	Approved
0.6882	Remote Similarity	NPD4788	Approved
0.6881	Remote Similarity	NPD4632	Approved
0.686	Remote Similarity	NPD4787	Phase 1
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6842	Remote Similarity	NPD6370	Approved
0.6832	Remote Similarity	NPD4755	Approved
0.6809	Remote Similarity	NPD4786	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6759	Remote Similarity	NPD4634	Approved
0.6754	Remote Similarity	NPD6016	Approved
0.6754	Remote Similarity	NPD6015	Approved
0.6733	Remote Similarity	NPD5222	Approved
0.6733	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD4697	Phase 3
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6724	Remote Similarity	NPD7492	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD4700	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6699	Remote Similarity	NPD8418	Phase 2
0.6698	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD5988	Approved
0.6695	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD5223	Approved
0.661	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD7078	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6602	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD4202	Approved
0.66	Remote Similarity	NPD6399	Phase 3
0.6596	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD8133	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6571	Remote Similarity	NPD5211	Phase 2
0.6559	Remote Similarity	NPD7525	Registered
0.6555	Remote Similarity	NPD6033	Approved
0.6549	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6920	Discontinued
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD5175	Approved
0.65	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD7604	Phase 2
0.6486	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD6940	Discontinued
0.6449	Remote Similarity	NPD5141	Approved
0.6415	Remote Similarity	NPD7632	Discontinued
0.6404	Remote Similarity	NPD7115	Discovery
0.6389	Remote Similarity	NPD4768	Approved
0.6389	Remote Similarity	NPD4767	Approved
0.6387	Remote Similarity	NPD6336	Discontinued
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD371	Approved
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD3133	Approved
0.6289	Remote Similarity	NPD3666	Approved
0.6289	Remote Similarity	NPD3665	Phase 1
0.6273	Remote Similarity	NPD5128	Approved
0.6273	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4730	Approved
0.6261	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6067	Discontinued
0.6207	Remote Similarity	NPD6335	Approved
0.619	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6274	Approved
0.6174	Remote Similarity	NPD6868	Approved
0.6162	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5250	Approved
0.6161	Remote Similarity	NPD5249	Phase 3
0.6161	Remote Similarity	NPD5169	Approved
0.6161	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5248	Approved
0.6161	Remote Similarity	NPD5251	Approved
0.6161	Remote Similarity	NPD5135	Approved
0.6161	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7991	Discontinued
0.6154	Remote Similarity	NPD7100	Approved
0.6146	Remote Similarity	NPD1780	Approved
0.6146	Remote Similarity	NPD1779	Approved
0.6126	Remote Similarity	NPD6415	Discontinued
0.6126	Remote Similarity	NPD5168	Approved
0.6122	Remote Similarity	NPD3668	Phase 3
0.6121	Remote Similarity	NPD6317	Approved
0.6106	Remote Similarity	NPD5217	Approved
0.6106	Remote Similarity	NPD5215	Approved
0.6106	Remote Similarity	NPD5216	Approved
0.6106	Remote Similarity	NPD5127	Approved
0.61	Remote Similarity	NPD7524	Approved
0.6083	Remote Similarity	NPD8328	Phase 3
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4221	Approved
0.6078	Remote Similarity	NPD6700	Approved
0.6078	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6314	Approved
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6068	Remote Similarity	NPD6313	Approved
0.6061	Remote Similarity	NPD5329	Approved
0.605	Remote Similarity	NPD6908	Approved
0.605	Remote Similarity	NPD6909	Approved
0.604	Remote Similarity	NPD6903	Approved
0.604	Remote Similarity	NPD6672	Approved
0.604	Remote Similarity	NPD5737	Approved
0.604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3669	Approved
0.6019	Remote Similarity	NPD6702	Approved
0.6019	Remote Similarity	NPD6703	Approved
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD7146	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