NPASS Compound

Structure

NPC472979 OpenBabel07101719522D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 0.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 0.8660 1.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 6 0 0 0 17 18 1 0 0 0 0 17 21 1 6 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	3.64
LogD:	2.88
LogS:	-4.364
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	3.567
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.616
MDCK Permeability:	1.4613167877541855e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.36
Plasma Protein Binding (PPB):	90.90658569335938%
Volume Distribution (VD):	1.411
Pgp-substrate:	10.409377098083496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.485
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	5.032
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.475
Carcinogencity:	0.026
Eye Corrosion:	0.014
Eye Irritation:	0.715
Respiratory Toxicity:	0.269

Download Data

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

Natural Product: NPC472979

Natural Product ID:	NPC472979
*Common Name:**	VXXSPOVQLBTGOO-HLIPFELVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VXXSPOVQLBTGOO-HLIPFELVSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-18(2)16-9-6-13-12-14(19(3,4)22)7-8-15(13)20(16,5)11-10-17(18)21/h7-8,12,16-17,21-22H,6,9-11H2,1-5H3/t16-,17-,20+/m1/s1
SMILES:	O[C@@H]1CC[C@@]2([C@@H](C1(C)C)CCc1c2ccc(c1)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594343
PubChem CID:	n.a.
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
NPO32900	chloranthus sessilifolius	Species	Chloranthaceae	Eukaryota	Whole plants	Fengqi Mountains, Sichuan Province, China	2012-Aug	PMID[26126961]

☑ 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
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17800.0	nM	PMID[537655]
NPT27	Others	Unspecified		Activity	=	95.4	%	PMID[537655]

☑ 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 NPC472979 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	238
0.1-0.2	1228
0.2-0.3	2368
0.3-0.4	7845
0.4-0.5	13259
0.5-0.6	13470
0.6-0.7	3730
0.7-0.8	444
0.8-0.85	70
0.85-0.9	34
0.9-0.95	2
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC27252
0.98	High Similarity	NPC472980
0.9798	High Similarity	NPC243601
0.9703	High Similarity	NPC149455
0.9703	High Similarity	NPC64642
0.9703	High Similarity	NPC472982
0.9596	High Similarity	NPC19856
0.9091	High Similarity	NPC324602
0.8991	High Similarity	NPC469663
0.8991	High Similarity	NPC92
0.8991	High Similarity	NPC472862
0.8879	High Similarity	NPC471188
0.8818	High Similarity	NPC38893
0.8818	High Similarity	NPC219112
0.8818	High Similarity	NPC477137
0.8818	High Similarity	NPC308311
0.875	High Similarity	NPC56168
0.8739	High Similarity	NPC477136
0.8727	High Similarity	NPC192948
0.8727	High Similarity	NPC147179
0.8727	High Similarity	NPC35797
0.8704	High Similarity	NPC111108
0.8684	High Similarity	NPC369
0.8684	High Similarity	NPC293831
0.8673	High Similarity	NPC234337
0.8673	High Similarity	NPC133389
0.8673	High Similarity	NPC183339
0.8661	High Similarity	NPC471671
0.8649	High Similarity	NPC308828
0.8636	High Similarity	NPC268160
0.8611	High Similarity	NPC133308
0.8586	High Similarity	NPC220596
0.8584	High Similarity	NPC469644
0.8571	High Similarity	NPC172219
0.8571	High Similarity	NPC304510
0.8534	High Similarity	NPC77691
0.8532	High Similarity	NPC471189
0.8496	Intermediate Similarity	NPC469609
0.8491	Intermediate Similarity	NPC471133
0.8482	Intermediate Similarity	NPC212891
0.8455	Intermediate Similarity	NPC228425
0.8448	Intermediate Similarity	NPC182333
0.8448	Intermediate Similarity	NPC273336
0.844	Intermediate Similarity	NPC475002
0.844	Intermediate Similarity	NPC95126
0.8393	Intermediate Similarity	NPC469719
0.8384	Intermediate Similarity	NPC1793
0.8364	Intermediate Similarity	NPC176279
0.8364	Intermediate Similarity	NPC260323
0.8333	Intermediate Similarity	NPC154030
0.8333	Intermediate Similarity	NPC48342
0.8333	Intermediate Similarity	NPC164649
0.8319	Intermediate Similarity	NPC253681
0.8319	Intermediate Similarity	NPC242764
0.8319	Intermediate Similarity	NPC105141
0.8319	Intermediate Similarity	NPC5486
0.8319	Intermediate Similarity	NPC471668
0.8318	Intermediate Similarity	NPC471186
0.8317	Intermediate Similarity	NPC128645
0.8304	Intermediate Similarity	NPC195922
0.8288	Intermediate Similarity	NPC250323
0.8286	Intermediate Similarity	NPC469481
0.8286	Intermediate Similarity	NPC289117
0.8276	Intermediate Similarity	NPC328504
0.8276	Intermediate Similarity	NPC472981
0.8273	Intermediate Similarity	NPC132720
0.8273	Intermediate Similarity	NPC141782
0.8224	Intermediate Similarity	NPC472222
0.8224	Intermediate Similarity	NPC315794
0.8224	Intermediate Similarity	NPC472221
0.819	Intermediate Similarity	NPC260832
0.819	Intermediate Similarity	NPC135467
0.8158	Intermediate Similarity	NPC154511
0.8158	Intermediate Similarity	NPC474358
0.8158	Intermediate Similarity	NPC257540
0.8158	Intermediate Similarity	NPC137496
0.8158	Intermediate Similarity	NPC474387
0.8158	Intermediate Similarity	NPC247858
0.8151	Intermediate Similarity	NPC181334
0.8142	Intermediate Similarity	NPC221275
0.8136	Intermediate Similarity	NPC152946
0.8136	Intermediate Similarity	NPC471794
0.8125	Intermediate Similarity	NPC46940
0.8108	Intermediate Similarity	NPC13482
0.8103	Intermediate Similarity	NPC126002
0.8103	Intermediate Similarity	NPC151197
0.8103	Intermediate Similarity	NPC93071
0.8091	Intermediate Similarity	NPC11554
0.8087	Intermediate Similarity	NPC45794
0.8083	Intermediate Similarity	NPC4286
0.8083	Intermediate Similarity	NPC76119
0.8081	Intermediate Similarity	NPC93843
0.8081	Intermediate Similarity	NPC474211
0.8073	Intermediate Similarity	NPC142326
0.8073	Intermediate Similarity	NPC94751
0.8067	Intermediate Similarity	NPC471187
0.8067	Intermediate Similarity	NPC307139
0.8053	Intermediate Similarity	NPC715
0.8051	Intermediate Similarity	NPC77569
0.8051	Intermediate Similarity	NPC142198
0.8039	Intermediate Similarity	NPC79917
0.8036	Intermediate Similarity	NPC322753
0.8036	Intermediate Similarity	NPC95716
0.8036	Intermediate Similarity	NPC77772
0.802	Intermediate Similarity	NPC199567
0.8017	Intermediate Similarity	NPC254233
0.8	Intermediate Similarity	NPC141001
0.8	Intermediate Similarity	NPC151477
0.7983	Intermediate Similarity	NPC478058
0.7983	Intermediate Similarity	NPC11250
0.7983	Intermediate Similarity	NPC71094
0.7982	Intermediate Similarity	NPC471534
0.7982	Intermediate Similarity	NPC117115
0.798	Intermediate Similarity	NPC474354
0.7961	Intermediate Similarity	NPC314690
0.7951	Intermediate Similarity	NPC471077
0.7949	Intermediate Similarity	NPC476645
0.7934	Intermediate Similarity	NPC87985
0.7934	Intermediate Similarity	NPC124030
0.7931	Intermediate Similarity	NPC16030
0.7917	Intermediate Similarity	NPC198014
0.7899	Intermediate Similarity	NPC253627
0.7899	Intermediate Similarity	NPC475166
0.7881	Intermediate Similarity	NPC68339
0.7879	Intermediate Similarity	NPC304538
0.7879	Intermediate Similarity	NPC168855
0.7876	Intermediate Similarity	NPC266937
0.7876	Intermediate Similarity	NPC470770
0.7869	Intermediate Similarity	NPC321822
0.7869	Intermediate Similarity	NPC325294
0.7863	Intermediate Similarity	NPC206
0.7857	Intermediate Similarity	NPC58865
0.784	Intermediate Similarity	NPC476847
0.7833	Intermediate Similarity	NPC321402
0.7826	Intermediate Similarity	NPC186933
0.7815	Intermediate Similarity	NPC259703
0.7815	Intermediate Similarity	NPC32322
0.7807	Intermediate Similarity	NPC177962
0.7807	Intermediate Similarity	NPC302371
0.7807	Intermediate Similarity	NPC62867
0.7805	Intermediate Similarity	NPC186889
0.7797	Intermediate Similarity	NPC323074
0.7787	Intermediate Similarity	NPC137750
0.7778	Intermediate Similarity	NPC172984
0.7768	Intermediate Similarity	NPC475006
0.7768	Intermediate Similarity	NPC262365
0.776	Intermediate Similarity	NPC196193
0.7759	Intermediate Similarity	NPC474486
0.775	Intermediate Similarity	NPC249340
0.775	Intermediate Similarity	NPC162935
0.7748	Intermediate Similarity	NPC21594
0.7748	Intermediate Similarity	NPC271274
0.7739	Intermediate Similarity	NPC317869
0.7739	Intermediate Similarity	NPC169616
0.7731	Intermediate Similarity	NPC318581
0.7731	Intermediate Similarity	NPC99734
0.7731	Intermediate Similarity	NPC325544
0.7731	Intermediate Similarity	NPC477037
0.7727	Intermediate Similarity	NPC475225
0.7727	Intermediate Similarity	NPC238696
0.7724	Intermediate Similarity	NPC43000
0.7724	Intermediate Similarity	NPC100414
0.7719	Intermediate Similarity	NPC151537
0.7706	Intermediate Similarity	NPC51015
0.7705	Intermediate Similarity	NPC10154
0.7705	Intermediate Similarity	NPC265413
0.7699	Intermediate Similarity	NPC314187
0.7698	Intermediate Similarity	NPC312341
0.7692	Intermediate Similarity	NPC470820
0.7686	Intermediate Similarity	NPC176208
0.7686	Intermediate Similarity	NPC121168
0.7679	Intermediate Similarity	NPC66834
0.7679	Intermediate Similarity	NPC320439
0.7677	Intermediate Similarity	NPC87299
0.7677	Intermediate Similarity	NPC99394
0.7677	Intermediate Similarity	NPC329319
0.7677	Intermediate Similarity	NPC103326
0.7672	Intermediate Similarity	NPC93181
0.7667	Intermediate Similarity	NPC241001
0.7661	Intermediate Similarity	NPC108164
0.7661	Intermediate Similarity	NPC30491
0.7661	Intermediate Similarity	NPC262936
0.7652	Intermediate Similarity	NPC471179
0.7647	Intermediate Similarity	NPC42657
0.7642	Intermediate Similarity	NPC275576
0.7638	Intermediate Similarity	NPC85595
0.7636	Intermediate Similarity	NPC235762
0.7636	Intermediate Similarity	NPC471228
0.7632	Intermediate Similarity	NPC296683
0.7632	Intermediate Similarity	NPC265513
0.7632	Intermediate Similarity	NPC44732
0.7627	Intermediate Similarity	NPC299180
0.7624	Intermediate Similarity	NPC99482
0.7623	Intermediate Similarity	NPC85511
0.7615	Intermediate Similarity	NPC72729
0.7615	Intermediate Similarity	NPC133809
0.7615	Intermediate Similarity	NPC294741
0.7615	Intermediate Similarity	NPC225079
0.7615	Intermediate Similarity	NPC136810
0.7615	Intermediate Similarity	NPC211885

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 NPC472979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	879
0.2-0.3	1188
0.3-0.4	2897
0.4-0.5	2280
0.5-0.6	1295
0.6-0.7	340
0.7-0.8	47
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD5700	Clinical (unspecified phase)
0.8545	High Similarity	NPD4869	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3091	Approved
0.8051	Intermediate Similarity	NPD3092	Approved
0.8034	Intermediate Similarity	NPD3095	Discontinued
0.8017	Intermediate Similarity	NPD7741	Discontinued
0.7838	Intermediate Similarity	NPD2342	Discontinued
0.7807	Intermediate Similarity	NPD7635	Approved
0.7787	Intermediate Similarity	NPD3094	Phase 2
0.7731	Intermediate Similarity	NPD4059	Approved
0.7731	Intermediate Similarity	NPD7725	Approved
0.7672	Intermediate Similarity	NPD5951	Approved
0.7607	Intermediate Similarity	NPD4198	Discontinued
0.7583	Intermediate Similarity	NPD3019	Approved
0.7523	Intermediate Similarity	NPD3020	Approved
0.7521	Intermediate Similarity	NPD2629	Approved
0.752	Intermediate Similarity	NPD5736	Approved
0.7438	Intermediate Similarity	NPD5126	Approved
0.7438	Intermediate Similarity	NPD2932	Approved
0.7438	Intermediate Similarity	NPD5125	Phase 3
0.7417	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1809	Phase 2
0.7383	Intermediate Similarity	NPD845	Approved
0.7339	Intermediate Similarity	NPD288	Approved
0.7315	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4624	Approved
0.7295	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6663	Approved
0.7266	Intermediate Similarity	NPD7008	Discontinued
0.7252	Intermediate Similarity	NPD4097	Suspended
0.725	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD844	Approved
0.7248	Intermediate Similarity	NPD2859	Approved
0.7248	Intermediate Similarity	NPD2860	Approved
0.7231	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3620	Phase 2
0.7231	Intermediate Similarity	NPD4140	Approved
0.7213	Intermediate Similarity	NPD1710	Approved
0.72	Intermediate Similarity	NPD5327	Phase 3
0.7179	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5735	Approved
0.7172	Intermediate Similarity	NPD9294	Approved
0.7167	Intermediate Similarity	NPD3317	Approved
0.7156	Intermediate Similarity	NPD2934	Approved
0.7156	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD2933	Approved
0.7156	Intermediate Similarity	NPD6049	Phase 2
0.7154	Intermediate Similarity	NPD2286	Discontinued
0.7143	Intermediate Similarity	NPD1616	Discontinued
0.7143	Intermediate Similarity	NPD7743	Approved
0.7143	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7742	Approved
0.7132	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6353	Approved
0.7119	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3023	Approved
0.7097	Intermediate Similarity	NPD3026	Approved
0.7094	Intermediate Similarity	NPD4750	Phase 3
0.7094	Intermediate Similarity	NPD3021	Approved
0.7094	Intermediate Similarity	NPD3022	Approved
0.708	Intermediate Similarity	NPD4817	Approved
0.708	Intermediate Similarity	NPD4818	Approved
0.7073	Intermediate Similarity	NPD4093	Discontinued
0.7073	Intermediate Similarity	NPD3025	Approved
0.7073	Intermediate Similarity	NPD3024	Approved
0.7069	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7715	Approved
0.7023	Intermediate Similarity	NPD7714	Approved
0.7018	Intermediate Similarity	NPD4231	Approved
0.7018	Intermediate Similarity	NPD4229	Approved
0.7016	Intermediate Similarity	NPD1751	Approved
0.7016	Intermediate Similarity	NPD4626	Approved
0.7016	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3638	Discontinued
0.693	Remote Similarity	NPD4719	Phase 2
0.6923	Remote Similarity	NPD2605	Approved
0.6923	Remote Similarity	NPD2606	Approved
0.6911	Remote Similarity	NPD7610	Discontinued
0.6891	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4625	Phase 3
0.687	Remote Similarity	NPD3682	Approved
0.687	Remote Similarity	NPD4658	Approved
0.687	Remote Similarity	NPD5155	Approved
0.687	Remote Similarity	NPD3680	Approved
0.687	Remote Similarity	NPD4656	Approved
0.687	Remote Similarity	NPD5156	Approved
0.6864	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2229	Approved
0.686	Remote Similarity	NPD2234	Approved
0.686	Remote Similarity	NPD2228	Approved
0.6846	Remote Similarity	NPD3635	Approved
0.6846	Remote Similarity	NPD3637	Approved
0.6846	Remote Similarity	NPD3636	Approved
0.6835	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1088	Approved
0.681	Remote Similarity	NPD3047	Approved
0.681	Remote Similarity	NPD3046	Approved
0.681	Remote Similarity	NPD1237	Approved
0.681	Remote Similarity	NPD3048	Approved
0.6807	Remote Similarity	NPD1792	Phase 2
0.6803	Remote Similarity	NPD497	Approved
0.68	Remote Similarity	NPD5691	Approved
0.6794	Remote Similarity	NPD3594	Approved
0.6794	Remote Similarity	NPD3595	Approved
0.6786	Remote Similarity	NPD7236	Approved
0.6769	Remote Similarity	NPD2194	Approved
0.6769	Remote Similarity	NPD2195	Approved
0.6763	Remote Similarity	NPD7003	Approved
0.6759	Remote Similarity	NPD1101	Approved
0.6754	Remote Similarity	NPD2066	Phase 3
0.675	Remote Similarity	NPD4253	Approved
0.675	Remote Similarity	NPD4254	Approved
0.6746	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4589	Approved
0.6744	Remote Similarity	NPD1283	Approved
0.6744	Remote Similarity	NPD6696	Suspended
0.6724	Remote Similarity	NPD3683	Approved
0.6724	Remote Similarity	NPD3681	Approved
0.6721	Remote Similarity	NPD495	Approved
0.6721	Remote Similarity	NPD496	Approved
0.6721	Remote Similarity	NPD6010	Discontinued
0.6721	Remote Similarity	NPD498	Approved
0.672	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2233	Approved
0.6719	Remote Similarity	NPD2232	Approved
0.6719	Remote Similarity	NPD2230	Approved
0.6716	Remote Similarity	NPD2238	Phase 2
0.6716	Remote Similarity	NPD4060	Phase 1
0.6696	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4814	Discontinued
0.6694	Remote Similarity	NPD7340	Approved
0.6692	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4721	Approved
0.6667	Remote Similarity	NPD6025	Phase 1
0.6667	Remote Similarity	NPD4726	Approved
0.6667	Remote Similarity	NPD9609	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD4725	Approved
0.6667	Remote Similarity	NPD9612	Approved
0.6667	Remote Similarity	NPD9495	Approved
0.6667	Remote Similarity	NPD9611	Approved
0.6667	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6586	Approved
0.6642	Remote Similarity	NPD6587	Approved
0.6641	Remote Similarity	NPD1201	Approved
0.6639	Remote Similarity	NPD7094	Approved
0.6639	Remote Similarity	NPD6858	Approved
0.6638	Remote Similarity	NPD846	Approved
0.6638	Remote Similarity	NPD854	Approved
0.6638	Remote Similarity	NPD855	Approved
0.6638	Remote Similarity	NPD940	Approved
0.6636	Remote Similarity	NPD1090	Approved
0.6636	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1089	Approved
0.6636	Remote Similarity	NPD1086	Approved
0.6613	Remote Similarity	NPD7157	Approved
0.6607	Remote Similarity	NPD3718	Approved
0.6607	Remote Similarity	NPD3719	Approved
0.6604	Remote Similarity	NPD3971	Phase 1
0.6591	Remote Similarity	NPD2861	Phase 2
0.6589	Remote Similarity	NPD7249	Approved
0.6589	Remote Similarity	NPD7250	Approved
0.6587	Remote Similarity	NPD5304	Approved
0.6587	Remote Similarity	NPD5303	Approved
0.6587	Remote Similarity	NPD7330	Discontinued
0.6585	Remote Similarity	NPD1398	Phase 1
0.6583	Remote Similarity	NPD4717	Approved
0.6583	Remote Similarity	NPD4718	Approved
0.6583	Remote Similarity	NPD4720	Approved
0.6581	Remote Similarity	NPD6647	Phase 2
0.6581	Remote Similarity	NPD1930	Approved
0.6581	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1929	Approved
0.6581	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3495	Discontinued
0.6573	Remote Similarity	NPD3645	Discontinued
0.6571	Remote Similarity	NPD6674	Discontinued
0.6569	Remote Similarity	NPD5886	Approved
0.6569	Remote Similarity	NPD41	Approved
0.6565	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4103	Phase 2
0.6562	Remote Similarity	NPD3896	Approved
0.6562	Remote Similarity	NPD3897	Approved
0.6562	Remote Similarity	NPD3895	Approved
0.6562	Remote Similarity	NPD3898	Approved
0.6555	Remote Similarity	NPD1445	Approved
0.6555	Remote Similarity	NPD1444	Approved
0.6552	Remote Similarity	NPD2553	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