NPASS Compound

Structure

NPC472144 OpenBabel07101719252D 36 42 0 0 1 0 0 0 0 0999 V2000 -1.5297 -0.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9753 0.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4906 0.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2464 -0.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0799 0.0272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 2.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0463 1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5459 0.8281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0860 1.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1449 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6792 1.9896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0860 -0.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4164 1.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2108 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9845 0.7364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5459 -0.7652 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3341 1.3406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5459 0.2970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6260 0.2970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8272 0.7691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2171 1.1084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0059 -0.4997 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3945 2.5966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0059 0.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0860 0.0315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6260 0.8281 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2108 1.1593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2941 0.6331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1643 1.8045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6930 0.0841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5459 -1.7346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8454 -0.9844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0822 3.5143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7750 -0.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3206 2.3099 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 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 6 0 0 0 16 22 1 0 0 0 0 16 31 1 6 0 0 0 17 13 1 6 0 0 0 17 35 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 20 30 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 32 1 6 0 0 0 23 29 1 0 0 0 0 23 33 2 0 0 0 0 23 35 1 0 0 0 0 25 4 1 1 0 0 0 26 27 1 6 0 0 0 27 6 1 6 0 0 0 28 7 1 1 0 0 0 28 36 1 0 0 0 0 29 11 1 6 0 0 0 30 34 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	517.646
LogP:	4.136
LogD:	4.149
LogS:	-4.72
# Rotatable Bonds:	0
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	6.862
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.19
MDCK Permeability:	4.323857865529135e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.712

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.242
Plasma Protein Binding (PPB):	89.9234848022461%
Volume Distribution (VD):	1.464
Pgp-substrate:	7.776082992553711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	4.155
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.339
Drug-inuced Liver Injury (DILI):	0.142
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.845
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.441
Carcinogencity:	0.028
Eye Corrosion:	0.036
Eye Irritation:	0.07
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: NPC472144

Natural Product ID:	NPC472144
*Common Name:**	AWSUWDUPKXUOTI-VNKXSMBYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AWSUWDUPKXUOTI-VNKXSMBYSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-15-17-13-29(23(33)35-17)11-10-27(6)20-21(29)28(15,7)36-30(20,34)14-19-25(4)12-16(31)22(32)24(2,3)18(25)8-9-26(19,27)5/h15-22,31-32,34H,8-14H2,1-7H3/t15-,16-,17+,18+,19-,20+,21-,22-,25+,26-,27-,28-,29-,30-/m1/s1
SMILES:	O[C@@H]1C[C@@]2(C)[C@H](C([C@@H]1O)(C)C)CC[C@@]1([C@@H]2C[C@@]2(O)O[C@]3([C@H]4[C@H]2[C@@]1(C)CC[C@]14C[C@@H]([C@H]3C)OC1=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342051
PubChem CID:	n.a.
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
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[570860]

☑ 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 NPC472144 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	474
0.1-0.2	3579
0.2-0.3	8628
0.3-0.4	13818
0.4-0.5	6620
0.5-0.6	4777
0.6-0.7	3060
0.7-0.8	1568
0.8-0.85	140
0.85-0.9	29
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC472145
0.9149	High Similarity	NPC235109
0.9043	High Similarity	NPC82633
0.9022	High Similarity	NPC18536
0.9022	High Similarity	NPC50443
0.9022	High Similarity	NPC185529
0.9022	High Similarity	NPC472146
0.8947	High Similarity	NPC163685
0.8947	High Similarity	NPC475785
0.8804	High Similarity	NPC476435
0.875	High Similarity	NPC475765
0.8723	High Similarity	NPC475878
0.8617	High Similarity	NPC470114
0.8571	High Similarity	NPC473299
0.8515	High Similarity	NPC100078
0.8431	Intermediate Similarity	NPC166079
0.835	Intermediate Similarity	NPC126753
0.8317	Intermediate Similarity	NPC244969
0.8317	Intermediate Similarity	NPC213528
0.8316	Intermediate Similarity	NPC67653
0.8316	Intermediate Similarity	NPC471459
0.8286	Intermediate Similarity	NPC470622
0.8283	Intermediate Similarity	NPC471241
0.8252	Intermediate Similarity	NPC306776
0.8247	Intermediate Similarity	NPC472147
0.8247	Intermediate Similarity	NPC472148
0.8242	Intermediate Similarity	NPC48756
0.8242	Intermediate Similarity	NPC271572
0.8242	Intermediate Similarity	NPC474870
0.8242	Intermediate Similarity	NPC280781
0.8242	Intermediate Similarity	NPC476071
0.8235	Intermediate Similarity	NPC225238
0.8224	Intermediate Similarity	NPC97002
0.8211	Intermediate Similarity	NPC476379
0.8211	Intermediate Similarity	NPC471221
0.8191	Intermediate Similarity	NPC83242
0.819	Intermediate Similarity	NPC154906
0.8182	Intermediate Similarity	NPC116683
0.8155	Intermediate Similarity	NPC327093
0.8148	Intermediate Similarity	NPC79193
0.8137	Intermediate Similarity	NPC471254
0.8137	Intermediate Similarity	NPC80640
0.8131	Intermediate Similarity	NPC157571
0.8119	Intermediate Similarity	NPC80417
0.8113	Intermediate Similarity	NPC471431
0.8105	Intermediate Similarity	NPC45833
0.8105	Intermediate Similarity	NPC110365
0.8105	Intermediate Similarity	NPC213658
0.8105	Intermediate Similarity	NPC62202
0.8105	Intermediate Similarity	NPC470920
0.81	Intermediate Similarity	NPC266417
0.81	Intermediate Similarity	NPC472273
0.8095	Intermediate Similarity	NPC207693
0.8085	Intermediate Similarity	NPC62572
0.8077	Intermediate Similarity	NPC158051
0.8077	Intermediate Similarity	NPC158367
0.8077	Intermediate Similarity	NPC119628
0.8065	Intermediate Similarity	NPC15091
0.8061	Intermediate Similarity	NPC475307
0.8019	Intermediate Similarity	NPC87393
0.8019	Intermediate Similarity	NPC22709
0.8	Intermediate Similarity	NPC138219
0.8	Intermediate Similarity	NPC203974
0.8	Intermediate Similarity	NPC475630
0.8	Intermediate Similarity	NPC475234
0.8	Intermediate Similarity	NPC40716
0.7982	Intermediate Similarity	NPC477465
0.7981	Intermediate Similarity	NPC267637
0.798	Intermediate Similarity	NPC470424
0.7979	Intermediate Similarity	NPC219535
0.7979	Intermediate Similarity	NPC25037
0.7979	Intermediate Similarity	NPC477434
0.7979	Intermediate Similarity	NPC34984
0.7979	Intermediate Similarity	NPC237938
0.7979	Intermediate Similarity	NPC18953
0.7963	Intermediate Similarity	NPC477489
0.7961	Intermediate Similarity	NPC470172
0.7957	Intermediate Similarity	NPC2096
0.7957	Intermediate Similarity	NPC208912
0.7944	Intermediate Similarity	NPC66513
0.7938	Intermediate Similarity	NPC61688
0.7935	Intermediate Similarity	NPC134227
0.7925	Intermediate Similarity	NPC473688
0.7925	Intermediate Similarity	NPC469826
0.7925	Intermediate Similarity	NPC262567
0.7925	Intermediate Similarity	NPC471626
0.7925	Intermediate Similarity	NPC231566
0.7917	Intermediate Similarity	NPC239938
0.7912	Intermediate Similarity	NPC472608
0.7909	Intermediate Similarity	NPC475490
0.7905	Intermediate Similarity	NPC273189
0.7905	Intermediate Similarity	NPC184805
0.7895	Intermediate Similarity	NPC131350
0.7895	Intermediate Similarity	NPC478111
0.7895	Intermediate Similarity	NPC477445
0.7885	Intermediate Similarity	NPC473406
0.7885	Intermediate Similarity	NPC34562
0.7885	Intermediate Similarity	NPC471253
0.7879	Intermediate Similarity	NPC182740
0.7879	Intermediate Similarity	NPC211845
0.7879	Intermediate Similarity	NPC122083
0.7879	Intermediate Similarity	NPC161035
0.7879	Intermediate Similarity	NPC256104
0.7872	Intermediate Similarity	NPC474253
0.7872	Intermediate Similarity	NPC213737
0.7872	Intermediate Similarity	NPC475820
0.7872	Intermediate Similarity	NPC269684
0.7872	Intermediate Similarity	NPC474346
0.7872	Intermediate Similarity	NPC474284
0.787	Intermediate Similarity	NPC469824
0.7864	Intermediate Similarity	NPC178853
0.7857	Intermediate Similarity	NPC88337
0.7857	Intermediate Similarity	NPC475211
0.785	Intermediate Similarity	NPC228190
0.785	Intermediate Similarity	NPC236753
0.7849	Intermediate Similarity	NPC475743
0.7838	Intermediate Similarity	NPC179429
0.7835	Intermediate Similarity	NPC473319
0.7835	Intermediate Similarity	NPC221993
0.7835	Intermediate Similarity	NPC131104
0.7835	Intermediate Similarity	NPC3032
0.783	Intermediate Similarity	NPC471430
0.7826	Intermediate Similarity	NPC73013
0.7822	Intermediate Similarity	NPC193785
0.7822	Intermediate Similarity	NPC476728
0.7822	Intermediate Similarity	NPC256227
0.7812	Intermediate Similarity	NPC80700
0.7812	Intermediate Similarity	NPC472272
0.7812	Intermediate Similarity	NPC155531
0.7812	Intermediate Similarity	NPC215968
0.78	Intermediate Similarity	NPC309127
0.78	Intermediate Similarity	NPC247877
0.7789	Intermediate Similarity	NPC105895
0.7789	Intermediate Similarity	NPC65133
0.7778	Intermediate Similarity	NPC474065
0.7767	Intermediate Similarity	NPC51579
0.7766	Intermediate Similarity	NPC154043
0.7766	Intermediate Similarity	NPC202688
0.7766	Intermediate Similarity	NPC477447
0.7766	Intermediate Similarity	NPC121121
0.7766	Intermediate Similarity	NPC470155
0.7766	Intermediate Similarity	NPC477446
0.7766	Intermediate Similarity	NPC60018
0.7757	Intermediate Similarity	NPC316930
0.7755	Intermediate Similarity	NPC24705
0.7755	Intermediate Similarity	NPC56962
0.7755	Intermediate Similarity	NPC477443
0.7755	Intermediate Similarity	NPC477440
0.7745	Intermediate Similarity	NPC470632
0.7742	Intermediate Similarity	NPC125366
0.7736	Intermediate Similarity	NPC215408
0.7732	Intermediate Similarity	NPC263802
0.7723	Intermediate Similarity	NPC305808
0.7723	Intermediate Similarity	NPC62407
0.7723	Intermediate Similarity	NPC287354
0.7717	Intermediate Similarity	NPC243594
0.7717	Intermediate Similarity	NPC31031
0.7714	Intermediate Similarity	NPC107385
0.7708	Intermediate Similarity	NPC476715
0.7708	Intermediate Similarity	NPC266651
0.77	Intermediate Similarity	NPC472232
0.77	Intermediate Similarity	NPC472231
0.77	Intermediate Similarity	NPC476189
0.7692	Intermediate Similarity	NPC477172
0.7685	Intermediate Similarity	NPC320475
0.7685	Intermediate Similarity	NPC321661
0.7677	Intermediate Similarity	NPC77756
0.7677	Intermediate Similarity	NPC477444
0.7677	Intermediate Similarity	NPC477442
0.7677	Intermediate Similarity	NPC477433
0.767	Intermediate Similarity	NPC471375
0.767	Intermediate Similarity	NPC253995
0.767	Intermediate Similarity	NPC209798
0.767	Intermediate Similarity	NPC471374
0.767	Intermediate Similarity	NPC211087
0.766	Intermediate Similarity	NPC470154
0.766	Intermediate Similarity	NPC470156
0.766	Intermediate Similarity	NPC50658
0.766	Intermediate Similarity	NPC58631
0.7653	Intermediate Similarity	NPC470872
0.7653	Intermediate Similarity	NPC236459
0.7647	Intermediate Similarity	NPC203434
0.7647	Intermediate Similarity	NPC237071
0.7647	Intermediate Similarity	NPC238796
0.7642	Intermediate Similarity	NPC88469
0.7642	Intermediate Similarity	NPC469827
0.7642	Intermediate Similarity	NPC301787
0.7636	Intermediate Similarity	NPC477492
0.7629	Intermediate Similarity	NPC248216
0.7629	Intermediate Similarity	NPC477283
0.7629	Intermediate Similarity	NPC471410
0.7629	Intermediate Similarity	NPC471411
0.7624	Intermediate Similarity	NPC477495
0.7609	Intermediate Similarity	NPC112463
0.7609	Intermediate Similarity	NPC307865
0.7604	Intermediate Similarity	NPC79308
0.76	Intermediate Similarity	NPC216137
0.7596	Intermediate Similarity	NPC471428
0.7596	Intermediate Similarity	NPC477656
0.7596	Intermediate Similarity	NPC471427

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 NPC472144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	513
0.1-0.2	3674
0.2-0.3	3320
0.3-0.4	991
0.4-0.5	337
0.5-0.6	212
0.6-0.7	93
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7642	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6114	Approved
0.734	Intermediate Similarity	NPD6115	Approved
0.734	Intermediate Similarity	NPD6697	Approved
0.734	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6116	Phase 1
0.7217	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1700	Approved
0.7128	Intermediate Similarity	NPD6117	Approved
0.7021	Intermediate Similarity	NPD3703	Phase 2
0.6957	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD8035	Phase 2
0.6915	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8328	Phase 3
0.6857	Remote Similarity	NPD8171	Discontinued
0.6837	Remote Similarity	NPD6928	Phase 2
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7507	Approved
0.672	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7736	Approved
0.6606	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD1779	Approved
0.66	Remote Similarity	NPD1780	Approved
0.6557	Remote Similarity	NPD6921	Approved
0.6555	Remote Similarity	NPD6940	Discontinued
0.6552	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7492	Approved
0.6526	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3702	Approved
0.6489	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7748	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6475	Remote Similarity	NPD6059	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6471	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3669	Approved
0.6449	Remote Similarity	NPD7515	Phase 2
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6421	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7516	Approved
0.6379	Remote Similarity	NPD7320	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6354	Remote Similarity	NPD5777	Approved
0.6348	Remote Similarity	NPD7128	Approved
0.6348	Remote Similarity	NPD6675	Approved
0.6348	Remote Similarity	NPD6008	Approved
0.6348	Remote Similarity	NPD6402	Approved
0.6348	Remote Similarity	NPD5739	Approved
0.633	Remote Similarity	NPD7900	Approved
0.633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6373	Approved
0.6325	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD7328	Approved
0.6311	Remote Similarity	NPD7327	Approved
0.6303	Remote Similarity	NPD6882	Approved
0.6293	Remote Similarity	NPD6412	Phase 2
0.6293	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8335	Approved
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD8296	Approved
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD6015	Approved
0.629	Remote Similarity	NPD8378	Approved
0.6261	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4244	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD4245	Approved
0.624	Remote Similarity	NPD5988	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6686	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.623	Remote Similarity	NPD6009	Approved
0.6218	Remote Similarity	NPD6649	Approved
0.6218	Remote Similarity	NPD6650	Approved
0.6211	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5360	Phase 3
0.621	Remote Similarity	NPD6319	Approved
0.621	Remote Similarity	NPD8294	Approved
0.621	Remote Similarity	NPD8377	Approved
0.6195	Remote Similarity	NPD7639	Approved
0.6195	Remote Similarity	NPD7640	Approved
0.6186	Remote Similarity	NPD6081	Approved
0.617	Remote Similarity	NPD4224	Phase 2
0.6167	Remote Similarity	NPD8297	Approved
0.616	Remote Similarity	NPD8516	Approved
0.616	Remote Similarity	NPD8033	Approved
0.616	Remote Similarity	NPD8515	Approved
0.616	Remote Similarity	NPD8517	Approved
0.616	Remote Similarity	NPD8513	Phase 3
0.6154	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD3698	Phase 2
0.6134	Remote Similarity	NPD7102	Approved
0.6134	Remote Similarity	NPD7290	Approved
0.6134	Remote Similarity	NPD6883	Approved
0.6129	Remote Similarity	NPD371	Approved
0.6091	Remote Similarity	NPD6399	Phase 3
0.6087	Remote Similarity	NPD7632	Discontinued
0.6083	Remote Similarity	NPD6847	Approved
0.6083	Remote Similarity	NPD8130	Phase 1
0.6083	Remote Similarity	NPD6617	Approved
0.6083	Remote Similarity	NPD6869	Approved
0.6082	Remote Similarity	NPD4789	Approved
0.6053	Remote Similarity	NPD8418	Phase 2
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6013	Approved
0.6042	Remote Similarity	NPD229	Approved
0.6	Remote Similarity	NPD6033	Approved
0.5982	Remote Similarity	NPD7991	Discontinued
0.598	Remote Similarity	NPD3671	Phase 1
0.5968	Remote Similarity	NPD7115	Discovery
0.5966	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7604	Phase 2
0.5906	Remote Similarity	NPD5983	Phase 2
0.59	Remote Similarity	NPD1811	Approved
0.59	Remote Similarity	NPD1810	Approved
0.5895	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4755	Approved
0.5868	Remote Similarity	NPD4634	Approved
0.5859	Remote Similarity	NPD4758	Discontinued
0.5846	Remote Similarity	NPD6336	Discontinued
0.5826	Remote Similarity	NPD4225	Approved
0.5825	Remote Similarity	NPD4238	Approved
0.5825	Remote Similarity	NPD4802	Phase 2
0.5825	Remote Similarity	NPD5364	Discontinued
0.582	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5328	Approved
0.5814	Remote Similarity	NPD6067	Discontinued
0.5812	Remote Similarity	NPD8086	Approved
0.5812	Remote Similarity	NPD8139	Approved
0.5812	Remote Similarity	NPD8085	Approved
0.5812	Remote Similarity	NPD8082	Approved
0.5812	Remote Similarity	NPD8084	Approved
0.5812	Remote Similarity	NPD8138	Approved
0.5812	Remote Similarity	NPD8083	Approved
0.5789	Remote Similarity	NPD7909	Approved
0.5781	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD7503	Approved
0.5776	Remote Similarity	NPD5285	Approved
0.5776	Remote Similarity	NPD5286	Approved
0.5776	Remote Similarity	NPD4700	Approved
0.5776	Remote Similarity	NPD4696	Approved
0.5769	Remote Similarity	NPD7645	Phase 2
0.5763	Remote Similarity	NPD8275	Approved
0.5763	Remote Similarity	NPD8276	Approved
0.576	Remote Similarity	NPD6274	Approved
0.5748	Remote Similarity	NPD7100	Approved
0.5748	Remote Similarity	NPD7101	Approved
0.5739	Remote Similarity	NPD6084	Phase 2
0.5739	Remote Similarity	NPD6083	Phase 2
0.5729	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8081	Approved
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD6079	Approved
0.5702	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3618	Phase 1
0.5682	Remote Similarity	NPD8074	Phase 3
0.5678	Remote Similarity	NPD5224	Approved
0.5678	Remote Similarity	NPD5225	Approved
0.5678	Remote Similarity	NPD4633	Approved
0.5678	Remote Similarity	NPD5211	Phase 2
0.5678	Remote Similarity	NPD5226	Approved
0.5669	Remote Similarity	NPD6335	Approved
0.5667	Remote Similarity	NPD8393	Approved
0.5659	Remote Similarity	NPD6908	Approved
0.5659	Remote Similarity	NPD6909	Approved
0.5652	Remote Similarity	NPD4697	Phase 3
0.5645	Remote Similarity	NPD6053	Discontinued
0.5636	Remote Similarity	NPD3573	Approved
0.563	Remote Similarity	NPD5175	Approved
0.563	Remote Similarity	NPD5174	Approved
0.56	Remote Similarity	NPD2687	Approved
0.56	Remote Similarity	NPD2254	Approved
0.56	Remote Similarity	NPD4787	Phase 1
0.56	Remote Similarity	NPD2686	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