NPASS Compound

Structure

NPC242767 OpenBabel07101718292D 25 26 0 0 1 0 0 0 0 0999 V2000 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 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 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 22 1 1 0 0 0 19 14 1 6 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 1 0 0 0 22 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.27
Volume:	390.417
LogP:	4.745
LogD:	3.909
LogS:	-4.534
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.323
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.352
MDCK Permeability:	1.8952316167997196e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	96.0127944946289%
Volume Distribution (VD):	1.294
Pgp-substrate:	3.6363391876220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.469
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.362
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	6.187
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.553
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.932
Carcinogencity:	0.072
Eye Corrosion:	0.455
Eye Irritation:	0.534
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC242767

Natural Product ID:	NPC242767
*Common Name:**	12-O-Acetylphysacoztomatin
IUPAC Name:	[(E,2R)-1-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-5-hydroxy-3-methylpent-3-en-2-yl] acetate
Synonyms:	12-O-Acetylphysacoztomatin
Standard InCHIKey:	XXKXYCZWYIZXHT-VWVWAGKGSA-N
Standard InCHI:	InChI=1S/C22H36O3/c1-15-8-9-20-21(4,5)11-7-12-22(20,6)18(15)14-19(25-17(3)24)16(2)10-13-23/h8,10,18-20,23H,7,9,11-14H2,1-6H3/b16-10+/t18-,19+,20-,22+/m0/s1
SMILES:	OC/C=C(/[C@@H](C[C@H]1C(=CC[C@@H]2[C@]1(C)CCCC2(C)C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172819
PubChem CID:	46873593
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	25.4	%	PMID[527818]

☑ 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 NPC242767 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	157
0.1-0.2	1145
0.2-0.3	4661
0.3-0.4	13967
0.4-0.5	9995
0.5-0.6	6885
0.6-0.7	4517
0.7-0.8	1275
0.8-0.85	73
0.85-0.9	19
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC35933
0.8861	High Similarity	NPC256112
0.8795	High Similarity	NPC246028
0.878	High Similarity	NPC166857
0.875	High Similarity	NPC311070
0.875	High Similarity	NPC23748
0.8649	High Similarity	NPC34834
0.8608	High Similarity	NPC233332
0.8571	High Similarity	NPC470734
0.8537	High Similarity	NPC42586
0.8537	High Similarity	NPC473251
0.8519	High Similarity	NPC42476
0.8519	High Similarity	NPC49208
0.85	High Similarity	NPC25554
0.85	High Similarity	NPC170303
0.8481	Intermediate Similarity	NPC100906
0.8471	Intermediate Similarity	NPC78973
0.8471	Intermediate Similarity	NPC220216
0.8462	Intermediate Similarity	NPC283619
0.8452	Intermediate Similarity	NPC24816
0.8434	Intermediate Similarity	NPC329692
0.8415	Intermediate Similarity	NPC102048
0.8415	Intermediate Similarity	NPC306951
0.8395	Intermediate Similarity	NPC471218
0.8391	Intermediate Similarity	NPC104925
0.8391	Intermediate Similarity	NPC298973
0.8375	Intermediate Similarity	NPC469802
0.8375	Intermediate Similarity	NPC281880
0.8372	Intermediate Similarity	NPC177641
0.8372	Intermediate Similarity	NPC234335
0.8372	Intermediate Similarity	NPC124374
0.8353	Intermediate Similarity	NPC20946
0.8353	Intermediate Similarity	NPC261320
0.8353	Intermediate Similarity	NPC473647
0.8333	Intermediate Similarity	NPC131329
0.8333	Intermediate Similarity	NPC312561
0.8313	Intermediate Similarity	NPC471795
0.8313	Intermediate Similarity	NPC109528
0.8293	Intermediate Similarity	NPC477124
0.8293	Intermediate Similarity	NPC476927
0.8293	Intermediate Similarity	NPC472377
0.8276	Intermediate Similarity	NPC115021
0.8276	Intermediate Similarity	NPC99653
0.8272	Intermediate Similarity	NPC142163
0.8272	Intermediate Similarity	NPC229584
0.8272	Intermediate Similarity	NPC14203
0.8272	Intermediate Similarity	NPC159148
0.8235	Intermediate Similarity	NPC472809
0.8235	Intermediate Similarity	NPC472810
0.8228	Intermediate Similarity	NPC40049
0.8214	Intermediate Similarity	NPC131813
0.8214	Intermediate Similarity	NPC471219
0.8214	Intermediate Similarity	NPC322159
0.8193	Intermediate Similarity	NPC165064
0.8182	Intermediate Similarity	NPC469697
0.8182	Intermediate Similarity	NPC472360
0.8182	Intermediate Similarity	NPC472416
0.8171	Intermediate Similarity	NPC155521
0.8171	Intermediate Similarity	NPC2524
0.8161	Intermediate Similarity	NPC329842
0.8161	Intermediate Similarity	NPC477574
0.8161	Intermediate Similarity	NPC477122
0.8158	Intermediate Similarity	NPC4299
0.814	Intermediate Similarity	NPC50488
0.814	Intermediate Similarity	NPC16265
0.814	Intermediate Similarity	NPC474396
0.814	Intermediate Similarity	NPC5509
0.8133	Intermediate Similarity	NPC476945
0.8125	Intermediate Similarity	NPC239098
0.8118	Intermediate Similarity	NPC245004
0.8118	Intermediate Similarity	NPC471779
0.8118	Intermediate Similarity	NPC471796
0.8111	Intermediate Similarity	NPC98112
0.8095	Intermediate Similarity	NPC191965
0.8095	Intermediate Similarity	NPC474013
0.8095	Intermediate Similarity	NPC52628
0.8095	Intermediate Similarity	NPC472442
0.8082	Intermediate Similarity	NPC329698
0.8072	Intermediate Similarity	NPC472440
0.8072	Intermediate Similarity	NPC474809
0.8072	Intermediate Similarity	NPC474789
0.8072	Intermediate Similarity	NPC52108
0.8068	Intermediate Similarity	NPC169343
0.8068	Intermediate Similarity	NPC53555
0.8052	Intermediate Similarity	NPC472254
0.8049	Intermediate Similarity	NPC475944
0.8049	Intermediate Similarity	NPC474683
0.8049	Intermediate Similarity	NPC474731
0.8049	Intermediate Similarity	NPC7505
0.8049	Intermediate Similarity	NPC474759
0.8049	Intermediate Similarity	NPC82986
0.8049	Intermediate Similarity	NPC474752
0.8049	Intermediate Similarity	NPC327002
0.8046	Intermediate Similarity	NPC469403
0.8046	Intermediate Similarity	NPC232426
0.8046	Intermediate Similarity	NPC198818
0.8046	Intermediate Similarity	NPC182136
0.8046	Intermediate Similarity	NPC48732
0.8046	Intermediate Similarity	NPC280149
0.8046	Intermediate Similarity	NPC221111
0.8046	Intermediate Similarity	NPC281942
0.8026	Intermediate Similarity	NPC471560
0.8026	Intermediate Similarity	NPC101622
0.8026	Intermediate Similarity	NPC474248
0.8025	Intermediate Similarity	NPC233295
0.8025	Intermediate Similarity	NPC44083
0.8025	Intermediate Similarity	NPC153987
0.8025	Intermediate Similarity	NPC327674
0.8023	Intermediate Similarity	NPC472378
0.8023	Intermediate Similarity	NPC474629
0.8	Intermediate Similarity	NPC284194
0.8	Intermediate Similarity	NPC474970
0.8	Intermediate Similarity	NPC211810
0.8	Intermediate Similarity	NPC286153
0.8	Intermediate Similarity	NPC175145
0.8	Intermediate Similarity	NPC262747
0.8	Intermediate Similarity	NPC84121
0.8	Intermediate Similarity	NPC88009
0.8	Intermediate Similarity	NPC137306
0.8	Intermediate Similarity	NPC471765
0.8	Intermediate Similarity	NPC162346
0.8	Intermediate Similarity	NPC190713
0.8	Intermediate Similarity	NPC69649
0.8	Intermediate Similarity	NPC220478
0.8	Intermediate Similarity	NPC475069
0.8	Intermediate Similarity	NPC132542
0.8	Intermediate Similarity	NPC325594
0.8	Intermediate Similarity	NPC473226
0.8	Intermediate Similarity	NPC221801
0.8	Intermediate Similarity	NPC68703
0.8	Intermediate Similarity	NPC114651
0.8	Intermediate Similarity	NPC91594
0.8	Intermediate Similarity	NPC82979
0.8	Intermediate Similarity	NPC102996
0.7978	Intermediate Similarity	NPC91010
0.7978	Intermediate Similarity	NPC469491
0.7978	Intermediate Similarity	NPC474922
0.7978	Intermediate Similarity	NPC105490
0.7976	Intermediate Similarity	NPC96055
0.7976	Intermediate Similarity	NPC46320
0.7955	Intermediate Similarity	NPC472814
0.7955	Intermediate Similarity	NPC177037
0.7955	Intermediate Similarity	NPC41239
0.7955	Intermediate Similarity	NPC472811
0.7955	Intermediate Similarity	NPC141831
0.7952	Intermediate Similarity	NPC224455
0.7952	Intermediate Similarity	NPC304285
0.7952	Intermediate Similarity	NPC471298
0.7952	Intermediate Similarity	NPC470049
0.7931	Intermediate Similarity	NPC293044
0.7931	Intermediate Similarity	NPC174342
0.7931	Intermediate Similarity	NPC472240
0.7931	Intermediate Similarity	NPC177141
0.7931	Intermediate Similarity	NPC281524
0.7931	Intermediate Similarity	NPC262858
0.7931	Intermediate Similarity	NPC146554
0.7931	Intermediate Similarity	NPC314727
0.7927	Intermediate Similarity	NPC195424
0.7927	Intermediate Similarity	NPC474592
0.7912	Intermediate Similarity	NPC254496
0.7912	Intermediate Similarity	NPC477719
0.7912	Intermediate Similarity	NPC210337
0.7912	Intermediate Similarity	NPC477718
0.7912	Intermediate Similarity	NPC473244
0.7907	Intermediate Similarity	NPC102640
0.7907	Intermediate Similarity	NPC171722
0.7901	Intermediate Similarity	NPC179028
0.7901	Intermediate Similarity	NPC321514
0.7901	Intermediate Similarity	NPC83351
0.7901	Intermediate Similarity	NPC209135
0.7901	Intermediate Similarity	NPC474816
0.7901	Intermediate Similarity	NPC476314
0.7901	Intermediate Similarity	NPC167891
0.7895	Intermediate Similarity	NPC96484
0.7895	Intermediate Similarity	NPC208999
0.7889	Intermediate Similarity	NPC472441
0.7889	Intermediate Similarity	NPC37603
0.7889	Intermediate Similarity	NPC471786
0.7889	Intermediate Similarity	NPC276110
0.7882	Intermediate Similarity	NPC119001
0.7882	Intermediate Similarity	NPC189311
0.7882	Intermediate Similarity	NPC266511
0.7882	Intermediate Similarity	NPC86316
0.7882	Intermediate Similarity	NPC106416
0.7882	Intermediate Similarity	NPC274448
0.7882	Intermediate Similarity	NPC30984
0.7875	Intermediate Similarity	NPC265588
0.7875	Intermediate Similarity	NPC247325
0.7875	Intermediate Similarity	NPC244488
0.7867	Intermediate Similarity	NPC202017
0.7867	Intermediate Similarity	NPC242945
0.7867	Intermediate Similarity	NPC259156
0.7865	Intermediate Similarity	NPC38232
0.7865	Intermediate Similarity	NPC472812
0.7865	Intermediate Similarity	NPC7349
0.7857	Intermediate Similarity	NPC193198
0.7857	Intermediate Similarity	NPC474193
0.7857	Intermediate Similarity	NPC57370
0.7857	Intermediate Similarity	NPC471297
0.7857	Intermediate Similarity	NPC79945

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 NPC242767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1456
0.2-0.3	3882
0.3-0.4	2420
0.4-0.5	809
0.5-0.6	276
0.6-0.7	152
0.7-0.8	9
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
0.7931	Intermediate Similarity	NPD6051	Approved
0.7742	Intermediate Similarity	NPD7640	Approved
0.7742	Intermediate Similarity	NPD7639	Approved
0.7634	Intermediate Similarity	NPD7638	Approved
0.7558	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4225	Approved
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7381	Intermediate Similarity	NPD7645	Phase 2
0.7368	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6942	Approved
0.7317	Intermediate Similarity	NPD8264	Approved
0.7317	Intermediate Similarity	NPD8039	Approved
0.7317	Intermediate Similarity	NPD7339	Approved
0.7283	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD1694	Approved
0.7229	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6903	Approved
0.7204	Intermediate Similarity	NPD7748	Approved
0.7174	Intermediate Similarity	NPD7515	Phase 2
0.7174	Intermediate Similarity	NPD7637	Suspended
0.7159	Intermediate Similarity	NPD4786	Approved
0.7126	Intermediate Similarity	NPD3667	Approved
0.7097	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD5779	Approved
0.7051	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6695	Phase 3
0.7041	Intermediate Similarity	NPD7632	Discontinued
0.7033	Intermediate Similarity	NPD6672	Approved
0.7033	Intermediate Similarity	NPD5737	Approved
0.6989	Remote Similarity	NPD6411	Approved
0.6988	Remote Similarity	NPD6924	Approved
0.6988	Remote Similarity	NPD6926	Approved
0.6979	Remote Similarity	NPD6084	Phase 2
0.6979	Remote Similarity	NPD7902	Approved
0.6979	Remote Similarity	NPD6083	Phase 2
0.6977	Remote Similarity	NPD6929	Approved
0.6966	Remote Similarity	NPD3665	Phase 1
0.6966	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3666	Approved
0.6966	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6930	Phase 2
0.6897	Remote Similarity	NPD6931	Approved
0.6897	Remote Similarity	NPD7525	Registered
0.6889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD368	Approved
0.6863	Remote Similarity	NPD6686	Approved
0.686	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6933	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD3618	Phase 1
0.6813	Remote Similarity	NPD6098	Approved
0.6809	Remote Similarity	NPD5693	Phase 1
0.6774	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6101	Approved
0.6774	Remote Similarity	NPD5328	Approved
0.6771	Remote Similarity	NPD5695	Phase 3
0.6768	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD342	Phase 1
0.6747	Remote Similarity	NPD4243	Approved
0.6744	Remote Similarity	NPD6925	Approved
0.6744	Remote Similarity	NPD5776	Phase 2
0.6739	Remote Similarity	NPD7524	Approved
0.6739	Remote Similarity	NPD7750	Discontinued
0.6707	Remote Similarity	NPD6923	Approved
0.6707	Remote Similarity	NPD6922	Approved
0.6705	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7514	Phase 3
0.6705	Remote Similarity	NPD7332	Phase 2
0.6703	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6632	Remote Similarity	NPD6079	Approved
0.663	Remote Similarity	NPD4623	Approved
0.663	Remote Similarity	NPD5279	Phase 3
0.663	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD6902	Approved
0.6627	Remote Similarity	NPD7143	Approved
0.6627	Remote Similarity	NPD7144	Approved
0.6596	Remote Similarity	NPD6080	Approved
0.6596	Remote Similarity	NPD6673	Approved
0.6596	Remote Similarity	NPD6904	Approved
0.6593	Remote Similarity	NPD3668	Phase 3
0.6591	Remote Similarity	NPD4195	Approved
0.6588	Remote Similarity	NPD4785	Approved
0.6588	Remote Similarity	NPD4784	Approved
0.6566	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD3573	Approved
0.6548	Remote Similarity	NPD7151	Approved
0.6548	Remote Similarity	NPD7150	Approved
0.6548	Remote Similarity	NPD7152	Approved
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6531	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD46	Approved
0.6526	Remote Similarity	NPD7838	Discovery
0.6526	Remote Similarity	NPD6698	Approved
0.6522	Remote Similarity	NPD6893	Approved
0.6517	Remote Similarity	NPD4819	Approved
0.6517	Remote Similarity	NPD4821	Approved
0.6517	Remote Similarity	NPD4822	Approved
0.6517	Remote Similarity	NPD4820	Approved
0.6517	Remote Similarity	NPD7509	Discontinued
0.6489	Remote Similarity	NPD5208	Approved
0.6484	Remote Similarity	NPD5332	Approved
0.6484	Remote Similarity	NPD5331	Approved
0.6477	Remote Similarity	NPD4271	Approved
0.6477	Remote Similarity	NPD4268	Approved
0.6476	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6373	Approved
0.6458	Remote Similarity	NPD6050	Approved
0.6458	Remote Similarity	NPD8035	Phase 2
0.6458	Remote Similarity	NPD8034	Phase 2
0.6458	Remote Similarity	NPD7087	Discontinued
0.6455	Remote Similarity	NPD7327	Approved
0.6455	Remote Similarity	NPD7328	Approved
0.6449	Remote Similarity	NPD6053	Discontinued
0.6447	Remote Similarity	NPD4219	Approved
0.6444	Remote Similarity	NPD4790	Discontinued
0.6444	Remote Similarity	NPD6898	Phase 1
0.6442	Remote Similarity	NPD5701	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7503	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.6421	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6883	Approved
0.6415	Remote Similarity	NPD7102	Approved
0.6415	Remote Similarity	NPD7290	Approved
0.64	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7516	Approved
0.6392	Remote Similarity	NPD4202	Approved
0.6381	Remote Similarity	NPD6011	Approved
0.6374	Remote Similarity	NPD4269	Approved
0.6374	Remote Similarity	NPD4223	Phase 3
0.6374	Remote Similarity	NPD4221	Approved
0.6374	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD6932	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6355	Remote Similarity	NPD6869	Approved
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD6847	Approved
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6650	Approved
0.6354	Remote Similarity	NPD5692	Phase 3
0.6354	Remote Similarity	NPD5207	Approved
0.6344	Remote Similarity	NPD5329	Approved
0.6339	Remote Similarity	NPD8294	Approved
0.6339	Remote Similarity	NPD8377	Approved
0.6337	Remote Similarity	NPD6404	Discontinued
0.6333	Remote Similarity	NPD4695	Discontinued
0.6333	Remote Similarity	NPD4748	Discontinued
0.6327	Remote Similarity	NPD5707	Approved
0.6322	Remote Similarity	NPD4190	Phase 3
0.6322	Remote Similarity	NPD5275	Approved
0.6321	Remote Similarity	NPD6014	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6296	Remote Similarity	NPD6882	Approved
0.6289	Remote Similarity	NPD5694	Approved
0.6289	Remote Similarity	NPD5281	Approved
0.6289	Remote Similarity	NPD5284	Approved
0.6286	Remote Similarity	NPD6412	Phase 2
0.6283	Remote Similarity	NPD8378	Approved
0.6283	Remote Similarity	NPD8380	Approved
0.6283	Remote Similarity	NPD8296	Approved
0.6283	Remote Similarity	NPD8033	Approved
0.6283	Remote Similarity	NPD8379	Approved
0.6283	Remote Similarity	NPD8335	Approved
0.6277	Remote Similarity	NPD5786	Approved
0.6263	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4197	Approved
0.6222	Remote Similarity	NPD6683	Phase 2

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