NPASS Compound

Structure

CID323421 OpenBabel06191716172D 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 3.4697 -0.2263 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 1 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 3.8765 -1.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 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 4.8710 -1.0354 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 12 1 0 0 0 0 8 14 1 0 0 0 0 9 14 1 0 0 0 0 9 23 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 5 1 6 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 14 24 1 1 0 0 0 15 13 1 6 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 2 0 0 0 0 17 30 1 1 0 0 0 18 19 1 0 0 0 0 18 31 1 1 0 0 0 19 23 1 6 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:	1.66
LogD:	0.865
LogS:	-1.872
# 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:	5.202
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:	-4.923
MDCK Permeability:	9.146211959887296e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	63.32828903198242%
Volume Distribution (VD):	0.763
Pgp-substrate:	58.15727615356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	9.319
Half-life (T1/2):	0.802

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.487
Skin Sensitization:	0.173
Carcinogencity:	0.155
Eye Corrosion:	0.173
Eye Irritation:	0.019
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC323421

Natural Product ID:	NPC323421
*Common Name:**	Cardivin D
IUPAC Name:	[(3aR,4S,6S,8S,10S,11S,11aR)-8,10-dihydroxy-6,10-dimethyl-3-methylidene-11-(2-methylpropanoyloxy)-2,5-dioxo-3a,4,6,7,8,9,11,11a-octahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate
Synonyms:	cardivin D
Standard InCHIKey:	WOJZAWJFEPVGSB-CHYAZBGWSA-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)9-14(24)8-12(5)16(17)25/h10-12,14-15,17-19,24,29H,6,8-9H2,1-5,7H3/t12-,14-,15-,17-,18+,19-,23-/m0/s1
SMILES:	O[C@H]1C[C@H](C)C(=O)[C@@H](OC(=O)C(C)C)[C@H]2[C@H]([C@@H]([C@@](C1)(C)O)OC(=O)C(C)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459018
PubChem CID:	21582601
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
NPO9396	Carpesium divaricatum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[9392887]
NPO9396	Carpesium divaricatum	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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.36	ug ml-1	PMID[468507]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.78	ug ml-1	PMID[468507]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	1.88	ug ml-1	PMID[468507]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.05	ug ml-1	PMID[468507]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[468507]

☑ 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 NPC323421 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	267
0.1-0.2	1963
0.2-0.3	6120
0.3-0.4	12021
0.4-0.5	12232
0.5-0.6	6912
0.6-0.7	2635
0.7-0.8	474
0.8-0.85	40
0.85-0.9	12
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328562
0.9889	High Similarity	NPC31645
0.9667	High Similarity	NPC190294
0.9574	High Similarity	NPC324017
0.9574	High Similarity	NPC320019
0.9468	High Similarity	NPC15993
0.9457	High Similarity	NPC158416
0.9457	High Similarity	NPC39859
0.9457	High Similarity	NPC470883
0.9457	High Similarity	NPC76862
0.8866	High Similarity	NPC476270
0.8842	High Similarity	NPC476009
0.8804	High Similarity	NPC474951
0.8804	High Similarity	NPC173926
0.8804	High Similarity	NPC92974
0.8737	High Similarity	NPC475900
0.8696	High Similarity	NPC177629
0.8696	High Similarity	NPC58219
0.8673	High Similarity	NPC201718
0.8617	High Similarity	NPC184463
0.8617	High Similarity	NPC329952
0.8617	High Similarity	NPC70251
0.8617	High Similarity	NPC475881
0.8587	High Similarity	NPC186148
0.8556	High Similarity	NPC128429
0.8542	High Similarity	NPC36954
0.8526	High Similarity	NPC476300
0.8485	Intermediate Similarity	NPC47880
0.8478	Intermediate Similarity	NPC475019
0.8478	Intermediate Similarity	NPC474762
0.8478	Intermediate Similarity	NPC474949
0.8478	Intermediate Similarity	NPC476015
0.8462	Intermediate Similarity	NPC151176
0.8462	Intermediate Similarity	NPC3464
0.8462	Intermediate Similarity	NPC474780
0.8462	Intermediate Similarity	NPC475963
0.8421	Intermediate Similarity	NPC30515
0.8416	Intermediate Similarity	NPC472756
0.8404	Intermediate Similarity	NPC307411
0.84	Intermediate Similarity	NPC149371
0.8387	Intermediate Similarity	NPC5130
0.837	Intermediate Similarity	NPC304509
0.837	Intermediate Similarity	NPC329749
0.837	Intermediate Similarity	NPC47958
0.837	Intermediate Similarity	NPC149725
0.8333	Intermediate Similarity	NPC212486
0.8333	Intermediate Similarity	NPC475912
0.8317	Intermediate Similarity	NPC472755
0.8316	Intermediate Similarity	NPC65359
0.8316	Intermediate Similarity	NPC51004
0.8298	Intermediate Similarity	NPC202672
0.8283	Intermediate Similarity	NPC471144
0.8283	Intermediate Similarity	NPC474213
0.8265	Intermediate Similarity	NPC476315
0.8252	Intermediate Similarity	NPC477513
0.8229	Intermediate Similarity	NPC12172
0.8229	Intermediate Similarity	NPC208886
0.8218	Intermediate Similarity	NPC472754
0.8218	Intermediate Similarity	NPC474747
0.82	Intermediate Similarity	NPC475949
0.8163	Intermediate Similarity	NPC270013
0.8163	Intermediate Similarity	NPC14961
0.8144	Intermediate Similarity	NPC81419
0.8144	Intermediate Similarity	NPC179746
0.8137	Intermediate Similarity	NPC475871
0.8137	Intermediate Similarity	NPC475873
0.8137	Intermediate Similarity	NPC475945
0.8125	Intermediate Similarity	NPC206614
0.8125	Intermediate Similarity	NPC329857
0.8125	Intermediate Similarity	NPC476004
0.8125	Intermediate Similarity	NPC469718
0.8125	Intermediate Similarity	NPC474761
0.8125	Intermediate Similarity	NPC474323
0.8119	Intermediate Similarity	NPC164598
0.8119	Intermediate Similarity	NPC472753
0.8119	Intermediate Similarity	NPC474339
0.8061	Intermediate Similarity	NPC81386
0.8061	Intermediate Similarity	NPC474035
0.8058	Intermediate Similarity	NPC472748
0.8041	Intermediate Similarity	NPC469627
0.8039	Intermediate Similarity	NPC471148
0.8	Intermediate Similarity	NPC474313
0.8	Intermediate Similarity	NPC190753
0.8	Intermediate Similarity	NPC471150
0.7981	Intermediate Similarity	NPC472749
0.7981	Intermediate Similarity	NPC472751
0.798	Intermediate Similarity	NPC163228
0.798	Intermediate Similarity	NPC474947
0.7961	Intermediate Similarity	NPC472747
0.7961	Intermediate Similarity	NPC472750
0.7959	Intermediate Similarity	NPC295204
0.7959	Intermediate Similarity	NPC273579
0.7959	Intermediate Similarity	NPC288240
0.7959	Intermediate Similarity	NPC162205
0.7959	Intermediate Similarity	NPC475302
0.7941	Intermediate Similarity	NPC185141
0.7941	Intermediate Similarity	NPC133907
0.7941	Intermediate Similarity	NPC46998
0.7941	Intermediate Similarity	NPC128733
0.7941	Intermediate Similarity	NPC110443
0.7941	Intermediate Similarity	NPC474742
0.7938	Intermediate Similarity	NPC475748
0.7938	Intermediate Similarity	NPC473619
0.7925	Intermediate Similarity	NPC38154
0.7921	Intermediate Similarity	NPC473326
0.79	Intermediate Similarity	NPC279621
0.79	Intermediate Similarity	NPC473859
0.7895	Intermediate Similarity	NPC470242
0.7885	Intermediate Similarity	NPC474741
0.7879	Intermediate Similarity	NPC303942
0.7879	Intermediate Similarity	NPC57405
0.7872	Intermediate Similarity	NPC138647
0.7872	Intermediate Similarity	NPC470238
0.7857	Intermediate Similarity	NPC473321
0.7843	Intermediate Similarity	NPC288876
0.7835	Intermediate Similarity	NPC474032
0.7835	Intermediate Similarity	NPC151770
0.7826	Intermediate Similarity	NPC474981
0.7812	Intermediate Similarity	NPC118601
0.7812	Intermediate Similarity	NPC179659
0.7812	Intermediate Similarity	NPC248602
0.781	Intermediate Similarity	NPC474101
0.78	Intermediate Similarity	NPC475659
0.78	Intermediate Similarity	NPC471142
0.7788	Intermediate Similarity	NPC473148
0.7788	Intermediate Similarity	NPC4620
0.7767	Intermediate Similarity	NPC264477
0.7767	Intermediate Similarity	NPC477511
0.7766	Intermediate Similarity	NPC11620
0.7766	Intermediate Similarity	NPC257358
0.7766	Intermediate Similarity	NPC474472
0.7755	Intermediate Similarity	NPC251385
0.7755	Intermediate Similarity	NPC49342
0.7736	Intermediate Similarity	NPC194620
0.7736	Intermediate Similarity	NPC72813
0.7736	Intermediate Similarity	NPC474421
0.7736	Intermediate Similarity	NPC324327
0.7736	Intermediate Similarity	NPC326994
0.7732	Intermediate Similarity	NPC178875
0.7732	Intermediate Similarity	NPC473715
0.7723	Intermediate Similarity	NPC476275
0.7723	Intermediate Similarity	NPC17585
0.7714	Intermediate Similarity	NPC220964
0.7714	Intermediate Similarity	NPC475676
0.7714	Intermediate Similarity	NPC100487
0.7708	Intermediate Similarity	NPC162071
0.7706	Intermediate Similarity	NPC66108
0.77	Intermediate Similarity	NPC474247
0.77	Intermediate Similarity	NPC121825
0.77	Intermediate Similarity	NPC71589
0.7677	Intermediate Similarity	NPC20713
0.767	Intermediate Similarity	NPC471381
0.767	Intermediate Similarity	NPC186861
0.7664	Intermediate Similarity	NPC233379
0.7664	Intermediate Similarity	NPC14862
0.7664	Intermediate Similarity	NPC327286
0.7664	Intermediate Similarity	NPC55972
0.7664	Intermediate Similarity	NPC169888
0.7664	Intermediate Similarity	NPC474664
0.7647	Intermediate Similarity	NPC111348
0.7647	Intermediate Similarity	NPC471140
0.7647	Intermediate Similarity	NPC40812
0.7642	Intermediate Similarity	NPC9303
0.7642	Intermediate Similarity	NPC44004
0.7642	Intermediate Similarity	NPC16313
0.7629	Intermediate Similarity	NPC231889
0.7624	Intermediate Similarity	NPC471141
0.7624	Intermediate Similarity	NPC322188
0.7624	Intermediate Similarity	NPC472873
0.7619	Intermediate Similarity	NPC475321
0.7619	Intermediate Similarity	NPC27687
0.7604	Intermediate Similarity	NPC21469
0.7604	Intermediate Similarity	NPC137033
0.76	Intermediate Similarity	NPC228451
0.76	Intermediate Similarity	NPC469692
0.76	Intermediate Similarity	NPC475838
0.76	Intermediate Similarity	NPC469645
0.76	Intermediate Similarity	NPC475788
0.76	Intermediate Similarity	NPC125674
0.7596	Intermediate Similarity	NPC473332
0.7593	Intermediate Similarity	NPC15218
0.7593	Intermediate Similarity	NPC475922
0.7589	Intermediate Similarity	NPC471145
0.7589	Intermediate Similarity	NPC471146
0.7576	Intermediate Similarity	NPC475855
0.7576	Intermediate Similarity	NPC179394
0.7576	Intermediate Similarity	NPC144133
0.7573	Intermediate Similarity	NPC187268
0.757	Intermediate Similarity	NPC26617
0.7551	Intermediate Similarity	NPC217983
0.7551	Intermediate Similarity	NPC153805
0.7551	Intermediate Similarity	NPC207114
0.7551	Intermediate Similarity	NPC474471
0.7551	Intermediate Similarity	NPC227379
0.7551	Intermediate Similarity	NPC281516
0.7549	Intermediate Similarity	NPC230800
0.7549	Intermediate Similarity	NPC477921
0.7549	Intermediate Similarity	NPC91771
0.7549	Intermediate Similarity	NPC142529
0.7547	Intermediate Similarity	NPC477510

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 NPC323421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	2690
0.2-0.3	3666
0.3-0.4	1615
0.4-0.5	554
0.5-0.6	254
0.6-0.7	43
0.7-0.8	2
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
0.757	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD46	Approved
0.74	Intermediate Similarity	NPD6698	Approved
0.7157	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7838	Discovery
0.7054	Intermediate Similarity	NPD6371	Approved
0.6952	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6686	Approved
0.6635	Remote Similarity	NPD1695	Approved
0.6606	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6319	Approved
0.6496	Remote Similarity	NPD8297	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6436	Remote Similarity	NPD6435	Approved
0.641	Remote Similarity	NPD6649	Approved
0.641	Remote Similarity	NPD6650	Approved
0.6406	Remote Similarity	NPD7260	Phase 2
0.6379	Remote Similarity	NPD6373	Approved
0.6379	Remote Similarity	NPD6372	Approved
0.6357	Remote Similarity	NPD6845	Suspended
0.6356	Remote Similarity	NPD6053	Discontinued
0.6341	Remote Similarity	NPD6921	Approved
0.6339	Remote Similarity	NPD5344	Discontinued
0.632	Remote Similarity	NPD7492	Approved
0.6306	Remote Similarity	NPD4225	Approved
0.6303	Remote Similarity	NPD4632	Approved
0.6303	Remote Similarity	NPD8133	Approved
0.6296	Remote Similarity	NPD5778	Approved
0.6296	Remote Similarity	NPD5779	Approved
0.6293	Remote Similarity	NPD6899	Approved
0.6293	Remote Similarity	NPD6881	Approved
0.629	Remote Similarity	NPD8080	Discontinued
0.627	Remote Similarity	NPD6616	Approved
0.6262	Remote Similarity	NPD5785	Approved
0.6261	Remote Similarity	NPD5739	Approved
0.6261	Remote Similarity	NPD6402	Approved
0.6261	Remote Similarity	NPD7128	Approved
0.6261	Remote Similarity	NPD6675	Approved
0.626	Remote Similarity	NPD6054	Approved
0.624	Remote Similarity	NPD7642	Approved
0.624	Remote Similarity	NPD8328	Phase 3
0.6238	Remote Similarity	NPD5368	Approved
0.623	Remote Similarity	NPD7641	Discontinued
0.622	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD7078	Approved
0.6218	Remote Similarity	NPD6882	Approved
0.6214	Remote Similarity	NPD7154	Phase 3
0.6214	Remote Similarity	NPD6110	Phase 1
0.621	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8444	Approved
0.621	Remote Similarity	NPD8267	Approved
0.621	Remote Similarity	NPD8269	Approved
0.621	Remote Similarity	NPD8268	Approved
0.621	Remote Similarity	NPD8266	Approved
0.6207	Remote Similarity	NPD5697	Approved
0.6196	Remote Similarity	NPD7909	Approved
0.619	Remote Similarity	NPD5786	Approved
0.6186	Remote Similarity	NPD7290	Approved
0.6186	Remote Similarity	NPD6883	Approved
0.6186	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD5369	Approved
0.6174	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7736	Approved
0.6161	Remote Similarity	NPD5696	Approved
0.616	Remote Similarity	NPD6370	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6148	Remote Similarity	NPD6009	Approved
0.6148	Remote Similarity	NPD7115	Discovery
0.6148	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7507	Approved
0.6134	Remote Similarity	NPD8130	Phase 1
0.6134	Remote Similarity	NPD6617	Approved
0.6134	Remote Similarity	NPD6847	Approved
0.6134	Remote Similarity	NPD6869	Approved
0.6132	Remote Similarity	NPD4250	Approved
0.6132	Remote Similarity	NPD4251	Approved
0.6129	Remote Similarity	NPD6059	Approved
0.6126	Remote Similarity	NPD7839	Suspended
0.6111	Remote Similarity	NPD7604	Phase 2
0.6102	Remote Similarity	NPD6012	Approved
0.6102	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD6014	Approved
0.6102	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5363	Approved
0.6094	Remote Similarity	NPD8293	Discontinued
0.608	Remote Similarity	NPD5983	Phase 2
0.608	Remote Similarity	NPD6016	Approved
0.608	Remote Similarity	NPD6015	Approved
0.6071	Remote Similarity	NPD6084	Phase 2
0.6071	Remote Similarity	NPD6083	Phase 2
0.6068	Remote Similarity	NPD5701	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4249	Approved
0.6032	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6011	Approved
0.6016	Remote Similarity	NPD8451	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD7319	Approved
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7829	Approved
0.5969	Remote Similarity	NPD8448	Approved
0.5965	Remote Similarity	NPD6648	Approved
0.5962	Remote Similarity	NPD4270	Approved
0.5962	Remote Similarity	NPD4269	Approved
0.5962	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6412	Phase 2
0.5922	Remote Similarity	NPD4820	Approved
0.5922	Remote Similarity	NPD4822	Approved
0.5922	Remote Similarity	NPD4819	Approved
0.5922	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4821	Approved
0.5909	Remote Similarity	NPD6411	Approved
0.5905	Remote Similarity	NPD5362	Discontinued
0.5893	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD7638	Approved
0.5868	Remote Similarity	NPD2204	Approved
0.5868	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6399	Phase 3
0.5852	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD8392	Approved
0.5833	Remote Similarity	NPD8390	Approved
0.5833	Remote Similarity	NPD8391	Approved
0.5833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7639	Approved
0.5826	Remote Similarity	NPD7640	Approved
0.5814	Remote Similarity	NPD8299	Approved
0.5814	Remote Similarity	NPD8342	Approved
0.5814	Remote Similarity	NPD8341	Approved
0.5814	Remote Similarity	NPD8340	Approved
0.5806	Remote Similarity	NPD6274	Approved
0.5798	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7101	Approved
0.5794	Remote Similarity	NPD1694	Approved
0.5794	Remote Similarity	NPD7100	Approved
0.5785	Remote Similarity	NPD4634	Approved
0.5778	Remote Similarity	NPD8415	Approved
0.5769	Remote Similarity	NPD8273	Phase 1
0.5769	Remote Similarity	NPD4252	Approved
0.5752	Remote Similarity	NPD4629	Approved
0.5752	Remote Similarity	NPD5210	Approved
0.5728	Remote Similarity	NPD4268	Approved
0.5728	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4271	Approved
0.5726	Remote Similarity	NPD8085	Approved
0.5726	Remote Similarity	NPD8139	Approved
0.5726	Remote Similarity	NPD8083	Approved
0.5726	Remote Similarity	NPD8138	Approved
0.5726	Remote Similarity	NPD8086	Approved
0.5726	Remote Similarity	NPD8084	Approved
0.5726	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD6335	Approved
0.569	Remote Similarity	NPD4696	Approved
0.569	Remote Similarity	NPD5285	Approved
0.569	Remote Similarity	NPD5286	Approved
0.5684	Remote Similarity	NPD3197	Phase 1
0.5682	Remote Similarity	NPD6033	Approved
0.5678	Remote Similarity	NPD8275	Approved
0.5678	Remote Similarity	NPD8276	Approved
0.566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4755	Approved
0.5641	Remote Similarity	NPD1700	Approved
0.5636	Remote Similarity	NPD5737	Approved
0.5636	Remote Similarity	NPD6672	Approved
0.5635	Remote Similarity	NPD6317	Approved
0.5631	Remote Similarity	NPD4756	Discovery
0.563	Remote Similarity	NPD5141	Approved
0.563	Remote Similarity	NPD8081	Approved
0.5625	Remote Similarity	NPD8035	Phase 2
0.5625	Remote Similarity	NPD7341	Phase 2
0.5625	Remote Similarity	NPD8034	Phase 2
0.5625	Remote Similarity	NPD5693	Phase 1

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