NPASS Compound

Structure

CID82633 OpenBabel06191715422D 34 40 0 0 1 0 0 0 0 0999 V2000 -3.9318 -0.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4441 -1.0885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7765 -2.1946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2888 -1.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2670 -2.6823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2670 1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2670 0.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9564 -0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9564 -3.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1117 -3.1699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1117 -0.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9564 0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4223 0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1117 1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4223 1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1117 -0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9564 -1.7069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2670 -0.2438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8011 -3.1699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4223 -2.1946 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2670 -1.7069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4223 -1.7069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4223 0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9564 -0.2438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8011 -2.1946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1117 -2.1946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2670 -0.7315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4223 -0.2438 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2670 0.7315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4223 -0.7315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6458 -3.6576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0653 1.5762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4223 -2.6823 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 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 1 0 0 0 18 29 1 6 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 33 1 6 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 30 1 6 0 0 0 22 33 1 0 0 0 0 23 29 1 0 0 0 0 23 32 2 0 0 0 0 23 34 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 30 1 6 0 0 0 29 14 1 1 0 0 0 30 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	500.065
LogP:	6.149
LogD:	4.862
LogS:	-6.005
# Rotatable Bonds:	0
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	6.383
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:	-5.298
MDCK Permeability:	2.383176797593478e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.376
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	90.72710418701172%
Volume Distribution (VD):	1.278
Pgp-substrate:	7.386337757110596%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	15.59
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.661
Human Hepatotoxicity (H-HT):	0.705
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.162
Carcinogencity:	0.137
Eye Corrosion:	0.07
Eye Irritation:	0.021
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC82633

Natural Product ID:	NPC82633
*Common Name:**	WBMXMSJTGDKFQT-DNWRIRKBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WBMXMSJTGDKFQT-DNWRIRKBSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-24(2)12-14-29-15-13-28(7)27(6)11-8-17-25(3,4)19(31)9-10-26(17,5)21(27)20-22(33-20)30(28,18(29)16-24)34-23(29)32/h17-22,31H,8-16H2,1-7H3/t17-,18+,19-,20-,21+,22-,26-,27+,28-,29-,30+/m0/s1
SMILES:	CC1(C)CC[C@]23CC[C@@]4(C)[C@]5(C)CC[C@H]6C(C)(C)[C@H](CC[C@]6(C)[C@H]5[C@H]5[C@@H]([C@@]4([C@@H]2C1)OC3=O)O5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465220
PubChem CID:	177092
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14533	Gomphrena macrocephala	Species	Amaranthaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125230]
NPO19352.1	Paeonia obovata var. japonica	Varieties	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO14533	Gomphrena macrocephala	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19352.1	Paeonia obovata var. japonica	Varieties	Paeoniaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	IC50	=	21000.0	nM	PMID[572660]
NPT140	Organism	Artemia	Artemia	LC50	>	700.0	ppm	PMID[572659]

☑ 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 NPC82633 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	476
0.1-0.2	3606
0.2-0.3	8595
0.3-0.4	14181
0.4-0.5	6224
0.5-0.6	4844
0.6-0.7	3657
0.7-0.8	1014
0.8-0.85	77
0.85-0.9	15
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC163685
0.9888	High Similarity	NPC235109
0.9326	High Similarity	NPC185529
0.9326	High Similarity	NPC472146
0.9043	High Similarity	NPC472144
0.8936	High Similarity	NPC472145
0.88	High Similarity	NPC154906
0.8696	High Similarity	NPC50443
0.8696	High Similarity	NPC18536
0.8681	High Similarity	NPC476379
0.8681	High Similarity	NPC476435
0.8652	High Similarity	NPC473299
0.8523	High Similarity	NPC476071
0.8523	High Similarity	NPC48756
0.8523	High Similarity	NPC280781
0.8495	Intermediate Similarity	NPC470114
0.8462	Intermediate Similarity	NPC83242
0.8387	Intermediate Similarity	NPC471459
0.8387	Intermediate Similarity	NPC67653
0.8352	Intermediate Similarity	NPC62572
0.8316	Intermediate Similarity	NPC472147
0.8316	Intermediate Similarity	NPC472148
0.8247	Intermediate Similarity	NPC475765
0.8247	Intermediate Similarity	NPC475785
0.8242	Intermediate Similarity	NPC237938
0.8242	Intermediate Similarity	NPC219535
0.8242	Intermediate Similarity	NPC477434
0.8229	Intermediate Similarity	NPC477495
0.8172	Intermediate Similarity	NPC470920
0.8152	Intermediate Similarity	NPC477445
0.8132	Intermediate Similarity	NPC227170
0.8132	Intermediate Similarity	NPC15091
0.8125	Intermediate Similarity	NPC474379
0.8119	Intermediate Similarity	NPC225238
0.8113	Intermediate Similarity	NPC97002
0.8105	Intermediate Similarity	NPC88337
0.8105	Intermediate Similarity	NPC475211
0.809	Intermediate Similarity	NPC73013
0.8085	Intermediate Similarity	NPC131104
0.8085	Intermediate Similarity	NPC471221
0.8085	Intermediate Similarity	NPC3032
0.8085	Intermediate Similarity	NPC473319
0.8061	Intermediate Similarity	NPC116683
0.8058	Intermediate Similarity	NPC126753
0.8043	Intermediate Similarity	NPC105895
0.8043	Intermediate Similarity	NPC25037
0.8043	Intermediate Similarity	NPC34984
0.8039	Intermediate Similarity	NPC327093
0.8021	Intermediate Similarity	NPC475878
0.8019	Intermediate Similarity	NPC477489
0.8	Intermediate Similarity	NPC472951
0.8	Intermediate Similarity	NPC470622
0.8	Intermediate Similarity	NPC24705
0.8	Intermediate Similarity	NPC61688
0.8	Intermediate Similarity	NPC56962
0.8	Intermediate Similarity	NPC472943
0.798	Intermediate Similarity	NPC471241
0.798	Intermediate Similarity	NPC266417
0.7978	Intermediate Similarity	NPC243594
0.7978	Intermediate Similarity	NPC472608
0.7978	Intermediate Similarity	NPC31031
0.7959	Intermediate Similarity	NPC17336
0.7957	Intermediate Similarity	NPC131350
0.7941	Intermediate Similarity	NPC34562
0.7935	Intermediate Similarity	NPC269684
0.7917	Intermediate Similarity	NPC77756
0.7912	Intermediate Similarity	NPC475743
0.7912	Intermediate Similarity	NPC271572
0.7912	Intermediate Similarity	NPC50658
0.7912	Intermediate Similarity	NPC474870
0.7895	Intermediate Similarity	NPC477614
0.7895	Intermediate Similarity	NPC226491
0.7879	Intermediate Similarity	NPC256227
0.7872	Intermediate Similarity	NPC302111
0.7872	Intermediate Similarity	NPC235196
0.7872	Intermediate Similarity	NPC228593
0.7872	Intermediate Similarity	NPC475729
0.7872	Intermediate Similarity	NPC80700
0.7872	Intermediate Similarity	NPC474215
0.7865	Intermediate Similarity	NPC143250
0.7865	Intermediate Similarity	NPC112463
0.7864	Intermediate Similarity	NPC100078
0.7857	Intermediate Similarity	NPC247877
0.7857	Intermediate Similarity	NPC309127
0.785	Intermediate Similarity	NPC157571
0.7843	Intermediate Similarity	NPC213528
0.7843	Intermediate Similarity	NPC244969
0.7843	Intermediate Similarity	NPC80640
0.7843	Intermediate Similarity	NPC471254
0.7835	Intermediate Similarity	NPC216137
0.783	Intermediate Similarity	NPC471431
0.7826	Intermediate Similarity	NPC61107
0.7826	Intermediate Similarity	NPC289486
0.7826	Intermediate Similarity	NPC477447
0.7826	Intermediate Similarity	NPC477446
0.7826	Intermediate Similarity	NPC470155
0.7822	Intermediate Similarity	NPC80417
0.7812	Intermediate Similarity	NPC477440
0.7812	Intermediate Similarity	NPC477443
0.781	Intermediate Similarity	NPC207693
0.781	Intermediate Similarity	NPC316930
0.7802	Intermediate Similarity	NPC125366
0.78	Intermediate Similarity	NPC472273
0.7789	Intermediate Similarity	NPC239938
0.7788	Intermediate Similarity	NPC119628
0.7788	Intermediate Similarity	NPC166079
0.7788	Intermediate Similarity	NPC306776
0.7788	Intermediate Similarity	NPC158051
0.7788	Intermediate Similarity	NPC158367
0.7778	Intermediate Similarity	NPC287354
0.7778	Intermediate Similarity	NPC470031
0.7778	Intermediate Similarity	NPC62407
0.7766	Intermediate Similarity	NPC477205
0.7766	Intermediate Similarity	NPC476715
0.7766	Intermediate Similarity	NPC473350
0.7755	Intermediate Similarity	NPC475307
0.7755	Intermediate Similarity	NPC476189
0.7736	Intermediate Similarity	NPC87393
0.7736	Intermediate Similarity	NPC310546
0.7736	Intermediate Similarity	NPC321661
0.7736	Intermediate Similarity	NPC320475
0.7736	Intermediate Similarity	NPC22709
0.7732	Intermediate Similarity	NPC477442
0.7732	Intermediate Similarity	NPC477433
0.7732	Intermediate Similarity	NPC477444
0.7727	Intermediate Similarity	NPC55508
0.7723	Intermediate Similarity	NPC475876
0.7717	Intermediate Similarity	NPC470156
0.7717	Intermediate Similarity	NPC58631
0.7717	Intermediate Similarity	NPC470154
0.7714	Intermediate Similarity	NPC40716
0.7714	Intermediate Similarity	NPC475630
0.7714	Intermediate Similarity	NPC138219
0.7714	Intermediate Similarity	NPC203974
0.7714	Intermediate Similarity	NPC475234
0.7708	Intermediate Similarity	NPC236459
0.7706	Intermediate Similarity	NPC477465
0.77	Intermediate Similarity	NPC477264
0.7692	Intermediate Similarity	NPC267637
0.7692	Intermediate Similarity	NPC201276
0.7692	Intermediate Similarity	NPC328737
0.7692	Intermediate Similarity	NPC301787
0.7692	Intermediate Similarity	NPC80891
0.7685	Intermediate Similarity	NPC477492
0.7684	Intermediate Similarity	NPC215968
0.7684	Intermediate Similarity	NPC155531
0.7684	Intermediate Similarity	NPC476717
0.7684	Intermediate Similarity	NPC472272
0.7684	Intermediate Similarity	NPC248216
0.7677	Intermediate Similarity	NPC470423
0.7677	Intermediate Similarity	NPC470424
0.767	Intermediate Similarity	NPC470172
0.7667	Intermediate Similarity	NPC307865
0.7664	Intermediate Similarity	NPC66513
0.766	Intermediate Similarity	NPC181871
0.766	Intermediate Similarity	NPC9060
0.766	Intermediate Similarity	NPC471044
0.766	Intermediate Similarity	NPC65133
0.766	Intermediate Similarity	NPC473336
0.7653	Intermediate Similarity	NPC52756
0.7647	Intermediate Similarity	NPC477655
0.7647	Intermediate Similarity	NPC477656
0.7642	Intermediate Similarity	NPC262567
0.7642	Intermediate Similarity	NPC473688
0.7642	Intermediate Similarity	NPC469826
0.7642	Intermediate Similarity	NPC231566
0.7642	Intermediate Similarity	NPC471626
0.7634	Intermediate Similarity	NPC268040
0.7634	Intermediate Similarity	NPC60018
0.7634	Intermediate Similarity	NPC2096
0.7634	Intermediate Similarity	NPC121121
0.7634	Intermediate Similarity	NPC202688
0.7634	Intermediate Similarity	NPC154043
0.7634	Intermediate Similarity	NPC208912
0.7624	Intermediate Similarity	NPC470425
0.7619	Intermediate Similarity	NPC200957
0.7619	Intermediate Similarity	NPC222833
0.7619	Intermediate Similarity	NPC273189
0.7619	Intermediate Similarity	NPC477877
0.7619	Intermediate Similarity	NPC138908
0.7619	Intermediate Similarity	NPC184805
0.7619	Intermediate Similarity	NPC470587
0.7609	Intermediate Similarity	NPC134227
0.7609	Intermediate Similarity	NPC261616
0.7609	Intermediate Similarity	NPC477851
0.7604	Intermediate Similarity	NPC263802
0.7604	Intermediate Similarity	NPC202937
0.7596	Intermediate Similarity	NPC471253
0.7596	Intermediate Similarity	NPC473406
0.7593	Intermediate Similarity	NPC474846
0.7593	Intermediate Similarity	NPC469824
0.7593	Intermediate Similarity	NPC469656
0.7593	Intermediate Similarity	NPC469655
0.7582	Intermediate Similarity	NPC171426
0.7582	Intermediate Similarity	NPC324700
0.7582	Intermediate Similarity	NPC80089
0.7582	Intermediate Similarity	NPC26029
0.7582	Intermediate Similarity	NPC34046
0.7582	Intermediate Similarity	NPC224802
0.7579	Intermediate Similarity	NPC474572

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 NPC82633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	506
0.1-0.2	3637
0.2-0.3	3361
0.3-0.4	995
0.4-0.5	341
0.5-0.6	214
0.6-0.7	83
0.7-0.8	13
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
0.7582	Intermediate Similarity	NPD6118	Approved
0.7582	Intermediate Similarity	NPD6114	Approved
0.7582	Intermediate Similarity	NPD6697	Approved
0.7582	Intermediate Similarity	NPD6115	Approved
0.7404	Intermediate Similarity	NPD1700	Approved
0.7363	Intermediate Similarity	NPD6117	Approved
0.7315	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7253	Intermediate Similarity	NPD3703	Phase 2
0.7196	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD8035	Phase 2
0.6957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3702	Approved
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6636	Remote Similarity	NPD7902	Approved
0.6635	Remote Similarity	NPD7515	Phase 2
0.6612	Remote Similarity	NPD8328	Phase 3
0.6583	Remote Similarity	NPD6921	Approved
0.6559	Remote Similarity	NPD5777	Approved
0.6522	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6008	Approved
0.6465	Remote Similarity	NPD1780	Approved
0.6465	Remote Similarity	NPD1779	Approved
0.6452	Remote Similarity	NPD4245	Approved
0.6452	Remote Similarity	NPD4244	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.6415	Remote Similarity	NPD8171	Discontinued
0.6413	Remote Similarity	NPD5360	Phase 3
0.6413	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7736	Approved
0.6387	Remote Similarity	NPD7115	Discovery
0.6383	Remote Similarity	NPD6081	Approved
0.6374	Remote Similarity	NPD4224	Phase 2
0.6372	Remote Similarity	NPD5739	Approved
0.6372	Remote Similarity	NPD6402	Approved
0.6372	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD6675	Approved
0.6371	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD6928	Phase 2
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6355	Remote Similarity	NPD7900	Approved
0.6355	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7319	Approved
0.6348	Remote Similarity	NPD6372	Approved
0.6348	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD3698	Phase 2
0.6337	Remote Similarity	NPD3669	Approved
0.6337	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8297	Approved
0.6303	Remote Similarity	NPD6940	Discontinued
0.629	Remote Similarity	NPD7492	Approved
0.6277	Remote Similarity	NPD4789	Approved
0.6271	Remote Similarity	NPD4632	Approved
0.6261	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD6899	Approved
0.6261	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.624	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.623	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD6059	Approved
0.623	Remote Similarity	NPD6319	Approved
0.6216	Remote Similarity	NPD8418	Phase 2
0.621	Remote Similarity	NPD7604	Phase 2
0.619	Remote Similarity	NPD7078	Approved
0.619	Remote Similarity	NPD8293	Discontinued
0.6174	Remote Similarity	NPD5697	Approved
0.6174	Remote Similarity	NPD5701	Approved
0.6162	Remote Similarity	NPD3671	Phase 1
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD371	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6129	Remote Similarity	NPD6370	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6105	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6847	Approved
0.6102	Remote Similarity	NPD8130	Phase 1
0.6102	Remote Similarity	NPD6617	Approved
0.6102	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6013	Approved
0.6068	Remote Similarity	NPD6014	Approved
0.6068	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6882	Approved
0.6048	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.6042	Remote Similarity	NPD4758	Discontinued
0.6034	Remote Similarity	NPD6412	Phase 2
0.6016	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5364	Discontinued
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5983	Remote Similarity	NPD6011	Approved
0.5983	Remote Similarity	NPD6686	Approved
0.5982	Remote Similarity	NPD4225	Approved
0.5981	Remote Similarity	NPD5328	Approved
0.5966	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD7645	Phase 2
0.5935	Remote Similarity	NPD7327	Approved
0.5935	Remote Similarity	NPD7328	Approved
0.592	Remote Similarity	NPD8335	Approved
0.592	Remote Similarity	NPD8516	Approved
0.592	Remote Similarity	NPD8378	Approved
0.592	Remote Similarity	NPD8379	Approved
0.592	Remote Similarity	NPD8515	Approved
0.592	Remote Similarity	NPD8517	Approved
0.592	Remote Similarity	NPD8296	Approved
0.592	Remote Similarity	NPD8513	Phase 3
0.592	Remote Similarity	NPD8380	Approved
0.5893	Remote Similarity	NPD6083	Phase 2
0.5893	Remote Similarity	NPD4755	Approved
0.5893	Remote Similarity	NPD6084	Phase 2
0.5872	Remote Similarity	NPD6411	Approved
0.5872	Remote Similarity	NPD6079	Approved
0.5856	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3618	Phase 1
0.584	Remote Similarity	NPD8294	Approved
0.584	Remote Similarity	NPD8377	Approved
0.5806	Remote Similarity	NPD7909	Approved
0.5804	Remote Similarity	NPD4697	Phase 3
0.5794	Remote Similarity	NPD8033	Approved
0.5794	Remote Similarity	NPD3573	Approved
0.5789	Remote Similarity	NPD5285	Approved
0.5789	Remote Similarity	NPD5286	Approved
0.5789	Remote Similarity	NPD4700	Approved
0.5789	Remote Similarity	NPD4696	Approved
0.5773	Remote Similarity	NPD4787	Phase 1
0.5772	Remote Similarity	NPD6274	Approved
0.5769	Remote Similarity	NPD6033	Approved
0.576	Remote Similarity	NPD7101	Approved
0.576	Remote Similarity	NPD7100	Approved
0.5758	Remote Similarity	NPD1811	Approved
0.5758	Remote Similarity	NPD1810	Approved
0.575	Remote Similarity	NPD4634	Approved
0.5741	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5344	Discontinued
0.5729	Remote Similarity	NPD229	Approved
0.5726	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4788	Approved
0.5702	Remote Similarity	NPD5696	Approved
0.569	Remote Similarity	NPD5225	Approved
0.569	Remote Similarity	NPD5224	Approved
0.569	Remote Similarity	NPD5211	Phase 2
0.569	Remote Similarity	NPD5226	Approved
0.569	Remote Similarity	NPD4633	Approved
0.5688	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6101	Approved
0.5686	Remote Similarity	NPD4802	Phase 2
0.5686	Remote Similarity	NPD4238	Approved
0.5682	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6335	Approved
0.5678	Remote Similarity	NPD6920	Discontinued
0.5676	Remote Similarity	NPD5779	Approved
0.5676	Remote Similarity	NPD5778	Approved
0.5669	Remote Similarity	NPD6909	Approved
0.5669	Remote Similarity	NPD6908	Approved
0.5669	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5222	Approved
0.5664	Remote Similarity	NPD5221	Approved
0.5664	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4786	Approved
0.5645	Remote Similarity	NPD6868	Approved
0.5641	Remote Similarity	NPD5175	Approved
0.5641	Remote Similarity	NPD5174	Approved
0.5619	Remote Similarity	NPD3667	Approved
0.5614	Remote Similarity	NPD5173	Approved
0.561	Remote Similarity	NPD8298	Phase 2
0.5603	Remote Similarity	NPD5223	Approved
0.56	Remote Similarity	NPD6317	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