NPASS Compound

Structure

NPC76862 OpenBabel07101718322D 32 33 0 0 1 0 0 0 0 0999 V2000 2.2238 -3.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -5.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3890 2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1933 2.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2947 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 2.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 1.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2129 0.4428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7230 -3.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 0.3782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2728 1.0168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 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 1.2024 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 6 13 2 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 5 1 1 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 24 2 0 0 0 0 15 13 1 1 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 1 0 0 0 17 30 1 6 0 0 0 18 19 1 0 0 0 0 18 31 1 6 0 0 0 19 23 1 1 0 0 0 19 32 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 27 2 0 0 0 0 21 32 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 23 7 1 6 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.22
Volume:	455.181
LogP:	2.033
LogD:	1.377
LogS:	-3.367
# Rotatable Bonds:	6
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	5.199
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.03
MDCK Permeability:	9.01459134183824e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	73.73410034179688%
Volume Distribution (VD):	1.036
Pgp-substrate:	37.00274658203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.151
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	5.841
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.194
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC76862

Natural Product ID:	NPC76862
*Common Name:**	4-Beta,9-Beta-Dihydroxy-5-Beta,8-Alpha-Di(Isobutyryloxy)-3-Oxo-Germacran-7-Beta,12-Alpha-Olide
IUPAC Name:	[(3aR,4R,5R,6R,10R,11R,11aS)-5,10-dihydroxy-6,10-dimethyl-3-methylidene-11-(2-methylpropanoyloxy)-2,9-dioxo-3a,4,5,6,7,8,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	WTBKTSVQJQEIHA-DQWWWAKVSA-N
Standard InCHI:	InChI=1S/C23H34O9/c1-10(2)20(26)30-17-15-13(6)22(28)31-18(15)19(32-21(27)11(3)4)23(7,29)14(24)9-8-12(5)16(17)25/h10-12,15-19,25,29H,6,8-9H2,1-5,7H3/t12-,15-,16-,17-,18+,19-,23+/m1/s1
SMILES:	O=C(C(C)C)O[C@H]1[C@H](O)[C@H](C)CCC(=O)[C@]([C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)OC(=O)C(C)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226924
PubChem CID:	16681337
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO29090	Carpesium triste	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[17432904]
NPO29090	Carpesium triste	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	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3.2	ug.mL-1	PMID[500162]
NPT27	Others	Unspecified		IC50	=	33.5	ug.mL-1	PMID[500162]
NPT27	Others	Unspecified		IC50	=	42.3	ug.mL-1	PMID[500162]

☑ 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 NPC76862 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	256
0.1-0.2	1913
0.2-0.3	5973
0.3-0.4	10333
0.4-0.5	13448
0.5-0.6	6980
0.6-0.7	3029
0.7-0.8	655
0.8-0.85	75
0.85-0.9	12
0.9-0.95	15
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC39859
1.0	High Similarity	NPC158416
1.0	High Similarity	NPC470883
0.9556	High Similarity	NPC190294
0.9457	High Similarity	NPC323421
0.9457	High Similarity	NPC328562
0.9348	High Similarity	NPC476009
0.9348	High Similarity	NPC31645
0.9239	High Similarity	NPC475900
0.9062	High Similarity	NPC320019
0.9062	High Similarity	NPC324017
0.8958	High Similarity	NPC15993
0.8958	High Similarity	NPC201718
0.8958	High Similarity	NPC47880
0.8901	High Similarity	NPC92974
0.8866	High Similarity	NPC149371
0.8791	High Similarity	NPC58219
0.8791	High Similarity	NPC177629
0.875	High Similarity	NPC471144
0.871	High Similarity	NPC184463
0.871	High Similarity	NPC475881
0.871	High Similarity	NPC70251
0.8696	High Similarity	NPC474951
0.8696	High Similarity	NPC173926
0.8681	High Similarity	NPC186148
0.8673	High Similarity	NPC474747
0.8632	High Similarity	NPC36954
0.8617	High Similarity	NPC476300
0.8602	High Similarity	NPC65359
0.8586	High Similarity	NPC475871
0.8586	High Similarity	NPC475945
0.8586	High Similarity	NPC472755
0.8571	High Similarity	NPC475019
0.8571	High Similarity	NPC474762
0.8571	High Similarity	NPC474949
0.8571	High Similarity	NPC476015
0.8556	High Similarity	NPC474780
0.8556	High Similarity	NPC151176
0.8556	High Similarity	NPC3464
0.8556	High Similarity	NPC475963
0.8515	High Similarity	NPC477513
0.8511	High Similarity	NPC30515
0.8511	High Similarity	NPC329952
0.8495	Intermediate Similarity	NPC307411
0.8485	Intermediate Similarity	NPC472754
0.8478	Intermediate Similarity	NPC5130
0.8469	Intermediate Similarity	NPC475949
0.8462	Intermediate Similarity	NPC329749
0.8462	Intermediate Similarity	NPC47958
0.8462	Intermediate Similarity	NPC304509
0.8462	Intermediate Similarity	NPC149725
0.8454	Intermediate Similarity	NPC474313
0.8444	Intermediate Similarity	NPC128429
0.8421	Intermediate Similarity	NPC212486
0.8421	Intermediate Similarity	NPC475912
0.8404	Intermediate Similarity	NPC51004
0.8387	Intermediate Similarity	NPC202672
0.8384	Intermediate Similarity	NPC472753
0.8384	Intermediate Similarity	NPC474742
0.8384	Intermediate Similarity	NPC474339
0.8384	Intermediate Similarity	NPC476270
0.8384	Intermediate Similarity	NPC164598
0.8367	Intermediate Similarity	NPC474213
0.8351	Intermediate Similarity	NPC473859
0.8351	Intermediate Similarity	NPC476315
0.8317	Intermediate Similarity	NPC474741
0.8317	Intermediate Similarity	NPC472756
0.8316	Intermediate Similarity	NPC208886
0.8316	Intermediate Similarity	NPC469627
0.8316	Intermediate Similarity	NPC12172
0.83	Intermediate Similarity	NPC471148
0.8283	Intermediate Similarity	NPC288876
0.8247	Intermediate Similarity	NPC475659
0.8247	Intermediate Similarity	NPC471142
0.8247	Intermediate Similarity	NPC270013
0.8247	Intermediate Similarity	NPC14961
0.8229	Intermediate Similarity	NPC81419
0.8229	Intermediate Similarity	NPC179746
0.8218	Intermediate Similarity	NPC4620
0.8218	Intermediate Similarity	NPC475873
0.8211	Intermediate Similarity	NPC474323
0.8211	Intermediate Similarity	NPC476004
0.8211	Intermediate Similarity	NPC474761
0.8211	Intermediate Similarity	NPC206614
0.82	Intermediate Similarity	NPC110443
0.82	Intermediate Similarity	NPC133907
0.82	Intermediate Similarity	NPC46998
0.82	Intermediate Similarity	NPC128733
0.82	Intermediate Similarity	NPC185141
0.8173	Intermediate Similarity	NPC38154
0.8144	Intermediate Similarity	NPC81386
0.8144	Intermediate Similarity	NPC474035
0.8137	Intermediate Similarity	NPC475676
0.8137	Intermediate Similarity	NPC100487
0.8137	Intermediate Similarity	NPC220964
0.8085	Intermediate Similarity	NPC190753
0.8081	Intermediate Similarity	NPC471150
0.8081	Intermediate Similarity	NPC40812
0.8061	Intermediate Similarity	NPC163228
0.8058	Intermediate Similarity	NPC474101
0.8041	Intermediate Similarity	NPC273579
0.8041	Intermediate Similarity	NPC162205
0.8041	Intermediate Similarity	NPC469645
0.8041	Intermediate Similarity	NPC295204
0.8041	Intermediate Similarity	NPC288240
0.8041	Intermediate Similarity	NPC469692
0.8041	Intermediate Similarity	NPC475788
0.8041	Intermediate Similarity	NPC475302
0.8021	Intermediate Similarity	NPC475748
0.8021	Intermediate Similarity	NPC473619
0.802	Intermediate Similarity	NPC264477
0.802	Intermediate Similarity	NPC477511
0.8	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC19841
0.7981	Intermediate Similarity	NPC26617
0.7981	Intermediate Similarity	NPC194620
0.7981	Intermediate Similarity	NPC72813
0.7981	Intermediate Similarity	NPC326994
0.7981	Intermediate Similarity	NPC474421
0.7981	Intermediate Similarity	NPC324327
0.798	Intermediate Similarity	NPC91771
0.798	Intermediate Similarity	NPC279621
0.798	Intermediate Similarity	NPC142529
0.798	Intermediate Similarity	NPC477921
0.798	Intermediate Similarity	NPC17585
0.798	Intermediate Similarity	NPC230800
0.7979	Intermediate Similarity	NPC470242
0.7961	Intermediate Similarity	NPC203659
0.7961	Intermediate Similarity	NPC472748
0.7959	Intermediate Similarity	NPC57405
0.7959	Intermediate Similarity	NPC121825
0.7959	Intermediate Similarity	NPC303942
0.7959	Intermediate Similarity	NPC473331
0.7957	Intermediate Similarity	NPC470238
0.7957	Intermediate Similarity	NPC138647
0.7941	Intermediate Similarity	NPC225353
0.7938	Intermediate Similarity	NPC20713
0.7938	Intermediate Similarity	NPC473321
0.7938	Intermediate Similarity	NPC184063
0.7917	Intermediate Similarity	NPC474032
0.7917	Intermediate Similarity	NPC151770
0.7912	Intermediate Similarity	NPC474981
0.7905	Intermediate Similarity	NPC474664
0.7905	Intermediate Similarity	NPC169888
0.7905	Intermediate Similarity	NPC233379
0.7905	Intermediate Similarity	NPC55972
0.7905	Intermediate Similarity	NPC14862
0.7905	Intermediate Similarity	NPC327286
0.79	Intermediate Similarity	NPC471140
0.79	Intermediate Similarity	NPC311904
0.7895	Intermediate Similarity	NPC118601
0.7895	Intermediate Similarity	NPC179659
0.7895	Intermediate Similarity	NPC248602
0.7885	Intermediate Similarity	NPC472751
0.7885	Intermediate Similarity	NPC9303
0.7885	Intermediate Similarity	NPC44004
0.7885	Intermediate Similarity	NPC472749
0.7885	Intermediate Similarity	NPC16313
0.7879	Intermediate Similarity	NPC477922
0.7879	Intermediate Similarity	NPC322188
0.7864	Intermediate Similarity	NPC69171
0.7864	Intermediate Similarity	NPC473148
0.7864	Intermediate Similarity	NPC474165
0.7864	Intermediate Similarity	NPC472747
0.7864	Intermediate Similarity	NPC472750
0.7864	Intermediate Similarity	NPC110989
0.7857	Intermediate Similarity	NPC308656
0.7857	Intermediate Similarity	NPC153590
0.7857	Intermediate Similarity	NPC473234
0.7857	Intermediate Similarity	NPC60386
0.7857	Intermediate Similarity	NPC473273
0.7857	Intermediate Similarity	NPC473263
0.7849	Intermediate Similarity	NPC11620
0.7849	Intermediate Similarity	NPC257358
0.7849	Intermediate Similarity	NPC474472
0.7835	Intermediate Similarity	NPC19087
0.7835	Intermediate Similarity	NPC316228
0.7835	Intermediate Similarity	NPC474232
0.783	Intermediate Similarity	NPC475922
0.783	Intermediate Similarity	NPC15218
0.783	Intermediate Similarity	NPC42662
0.7822	Intermediate Similarity	NPC255592
0.7822	Intermediate Similarity	NPC161855
0.7822	Intermediate Similarity	NPC187761
0.7822	Intermediate Similarity	NPC308567
0.7822	Intermediate Similarity	NPC83895
0.7822	Intermediate Similarity	NPC261377
0.7818	Intermediate Similarity	NPC471145
0.7818	Intermediate Similarity	NPC471146
0.7812	Intermediate Similarity	NPC53158
0.7812	Intermediate Similarity	NPC473715
0.7812	Intermediate Similarity	NPC178875
0.7789	Intermediate Similarity	NPC475491
0.7789	Intermediate Similarity	NPC469626
0.7789	Intermediate Similarity	NPC162071
0.7788	Intermediate Similarity	NPC477510
0.7788	Intermediate Similarity	NPC471143
0.7778	Intermediate Similarity	NPC474247
0.7778	Intermediate Similarity	NPC471147
0.7778	Intermediate Similarity	NPC71589

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 NPC76862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	2634
0.2-0.3	3653
0.3-0.4	1631
0.4-0.5	585
0.5-0.6	279
0.6-0.7	45
0.7-0.8	5
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
0.7981	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7983	Approved
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6698	Approved
0.7475	Intermediate Similarity	NPD46	Approved
0.7431	Intermediate Similarity	NPD6371	Approved
0.7353	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7838	Discovery
0.6923	Remote Similarity	NPD5282	Discontinued
0.6807	Remote Similarity	NPD8516	Approved
0.6807	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD8515	Approved
0.6807	Remote Similarity	NPD8517	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6723	Remote Similarity	NPD6319	Approved
0.6699	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6635	Remote Similarity	NPD5785	Approved
0.6589	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5786	Approved
0.6566	Remote Similarity	NPD5369	Approved
0.6557	Remote Similarity	NPD7642	Approved
0.6532	Remote Similarity	NPD8074	Phase 3
0.6529	Remote Similarity	NPD8267	Approved
0.6529	Remote Similarity	NPD8268	Approved
0.6529	Remote Similarity	NPD8269	Approved
0.6529	Remote Similarity	NPD8266	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD6435	Approved
0.6481	Remote Similarity	NPD7839	Suspended
0.6475	Remote Similarity	NPD8080	Discontinued
0.6471	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD5363	Approved
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6423	Remote Similarity	NPD8328	Phase 3
0.641	Remote Similarity	NPD8297	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD7078	Approved
0.6396	Remote Similarity	NPD5344	Discontinued
0.6393	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4632	Approved
0.6356	Remote Similarity	NPD8133	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6341	Remote Similarity	NPD6370	Approved
0.6337	Remote Similarity	NPD4269	Approved
0.6337	Remote Similarity	NPD4270	Approved
0.6337	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.632	Remote Similarity	NPD8451	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD5368	Approved
0.6299	Remote Similarity	NPD7319	Approved
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6373	Approved
0.629	Remote Similarity	NPD7829	Approved
0.629	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD7641	Discontinued
0.6275	Remote Similarity	NPD7154	Phase 3
0.627	Remote Similarity	NPD8448	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6262	Remote Similarity	NPD6411	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD8444	Approved
0.626	Remote Similarity	NPD6015	Approved
0.6228	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD6881	Approved
0.6207	Remote Similarity	NPD6899	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.6198	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD4251	Approved
0.619	Remote Similarity	NPD7507	Approved
0.6174	Remote Similarity	NPD6402	Approved
0.6174	Remote Similarity	NPD5739	Approved
0.6174	Remote Similarity	NPD7128	Approved
0.6174	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4252	Approved
0.6134	Remote Similarity	NPD6882	Approved
0.6124	Remote Similarity	NPD8390	Approved
0.6124	Remote Similarity	NPD8391	Approved
0.6124	Remote Similarity	NPD8392	Approved
0.6121	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD6110	Phase 1
0.6111	Remote Similarity	NPD8299	Approved
0.6111	Remote Similarity	NPD8340	Approved
0.6111	Remote Similarity	NPD8342	Approved
0.6111	Remote Similarity	NPD8341	Approved
0.6102	Remote Similarity	NPD7290	Approved
0.6102	Remote Similarity	NPD4634	Approved
0.6102	Remote Similarity	NPD6883	Approved
0.6102	Remote Similarity	NPD7102	Approved
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4249	Approved
0.6087	Remote Similarity	NPD7909	Approved
0.6068	Remote Similarity	NPD7320	Approved
0.6066	Remote Similarity	NPD6009	Approved
0.6063	Remote Similarity	NPD8273	Phase 1
0.6053	Remote Similarity	NPD8083	Approved
0.6053	Remote Similarity	NPD8084	Approved
0.6053	Remote Similarity	NPD8085	Approved
0.6053	Remote Similarity	NPD8138	Approved
0.6053	Remote Similarity	NPD8086	Approved
0.6053	Remote Similarity	NPD8139	Approved
0.6053	Remote Similarity	NPD8082	Approved
0.605	Remote Similarity	NPD8130	Phase 1
0.605	Remote Similarity	NPD6847	Approved
0.605	Remote Similarity	NPD2204	Approved
0.605	Remote Similarity	NPD6869	Approved
0.605	Remote Similarity	NPD6617	Approved
0.6032	Remote Similarity	NPD7604	Phase 2
0.6018	Remote Similarity	NPD6648	Approved
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6013	Approved
0.6015	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8275	Approved
0.6	Remote Similarity	NPD8276	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.5983	Remote Similarity	NPD6412	Phase 2
0.5983	Remote Similarity	NPD5701	Approved
0.5982	Remote Similarity	NPD6083	Phase 2
0.5982	Remote Similarity	NPD6084	Phase 2
0.598	Remote Similarity	NPD4819	Approved
0.598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4820	Approved
0.598	Remote Similarity	NPD4822	Approved
0.598	Remote Similarity	NPD4821	Approved
0.5962	Remote Similarity	NPD5362	Discontinued
0.5948	Remote Similarity	NPD8081	Approved
0.594	Remote Similarity	NPD8415	Approved
0.5938	Remote Similarity	NPD6336	Discontinued
0.5932	Remote Similarity	NPD6011	Approved
0.5929	Remote Similarity	NPD7638	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.5897	Remote Similarity	NPD6008	Approved
0.5897	Remote Similarity	NPD8393	Approved
0.5882	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7639	Approved
0.5877	Remote Similarity	NPD7640	Approved
0.5849	Remote Similarity	NPD1694	Approved
0.5847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6033	Approved
0.5843	Remote Similarity	NPD73	Approved
0.5826	Remote Similarity	NPD1700	Approved
0.5818	Remote Similarity	NPD7637	Suspended
0.5806	Remote Similarity	NPD7500	Approved
0.5804	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD5696	Approved
0.5785	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4271	Approved
0.5784	Remote Similarity	NPD4802	Phase 2
0.5784	Remote Similarity	NPD4268	Approved
0.5784	Remote Similarity	NPD4238	Approved
0.578	Remote Similarity	NPD5370	Suspended
0.5776	Remote Similarity	NPD5211	Phase 2
0.5745	Remote Similarity	NPD3197	Phase 1
0.5739	Remote Similarity	NPD4696	Approved
0.5739	Remote Similarity	NPD5286	Approved
0.5739	Remote Similarity	NPD5285	Approved
0.5729	Remote Similarity	NPD896	Approved
0.5729	Remote Similarity	NPD897	Approved
0.5729	Remote Similarity	NPD898	Approved
0.5726	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD5209	Approved
0.5702	Remote Similarity	NPD4755	Approved
0.5684	Remote Similarity	NPD7341	Phase 2
0.5678	Remote Similarity	NPD5141	Approved
0.5676	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8035	Phase 2
0.5676	Remote Similarity	NPD8034	Phase 2
0.5641	Remote Similarity	NPD5225	Approved
0.5641	Remote Similarity	NPD5226	Approved
0.5641	Remote Similarity	NPD5224	Approved
0.5641	Remote Similarity	NPD4633	Approved
0.5639	Remote Similarity	NPD5956	Approved
0.5635	Remote Similarity	NPD6335	Approved
0.5635	Remote Similarity	NPD7327	Approved
0.5635	Remote Similarity	NPD7328	Approved
0.5625	Remote Similarity	NPD8033	Approved
0.5625	Remote Similarity	NPD7503	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