NPASS Compound

Structure

NPC471222 OpenBabel07101718252D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.7796 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2796 2.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0475 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 0.1229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1473 -0.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8904 0.5841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2518 -1.0796 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 14 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 6 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 18 20 1 6 0 0 0 19 10 1 6 0 0 0 19 23 1 0 0 0 0 20 11 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	4.664
LogD:	3.968
LogS:	-4.967
# Rotatable Bonds:	0
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	5.435
Fsp3:	0.85
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:	-4.854
MDCK Permeability:	2.2616501155425794e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	91.4518814086914%
Volume Distribution (VD):	1.127
Pgp-substrate:	8.358101844787598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.404
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	9.685
Half-life (T1/2):	0.126

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.816
Skin Sensitization:	0.123
Carcinogencity:	0.783
Eye Corrosion:	0.011
Eye Irritation:	0.187
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC471222

Natural Product ID:	NPC471222
*Common Name:**	QEPRSDWQVDZILJ-QRKUABHPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QEPRSDWQVDZILJ-QRKUABHPSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-6-7-15-17(2,3)8-5-9-18(15,4)20(14)11-10-19(23-20)12-16(21)22-13-19/h7,14H,5-6,8-13H2,1-4H3/t14-,18+,19+,20-/m1/s1
SMILES:	O=C1OC[C@@]2(C1)CC[C@@]1(O2)[C@H](C)CC=C2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2391696
PubChem CID:	71579375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT994	Cell Line	ZR-75-30	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468725]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468725]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468725]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[468725]

☑ 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 NPC471222 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	206
0.1-0.2	1267
0.2-0.3	5757
0.3-0.4	14223
0.4-0.5	8249
0.5-0.6	7447
0.6-0.7	5189
0.7-0.8	351
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8182	Intermediate Similarity	NPC472655
0.8152	Intermediate Similarity	NPC15059
0.8081	Intermediate Similarity	NPC146731
0.8023	Intermediate Similarity	NPC35574
0.8	Intermediate Similarity	NPC41017
0.7979	Intermediate Similarity	NPC475657
0.7955	Intermediate Similarity	NPC475951
0.7905	Intermediate Similarity	NPC117712
0.79	Intermediate Similarity	NPC296950
0.7889	Intermediate Similarity	NPC100391
0.7841	Intermediate Similarity	NPC195424
0.783	Intermediate Similarity	NPC207217
0.7802	Intermediate Similarity	NPC470223
0.7789	Intermediate Similarity	NPC477615
0.7753	Intermediate Similarity	NPC475665
0.7742	Intermediate Similarity	NPC477128
0.7732	Intermediate Similarity	NPC469528
0.7732	Intermediate Similarity	NPC469369
0.7723	Intermediate Similarity	NPC471293
0.7717	Intermediate Similarity	NPC6979
0.7714	Intermediate Similarity	NPC269530
0.7714	Intermediate Similarity	NPC265391
0.7708	Intermediate Similarity	NPC250075
0.7708	Intermediate Similarity	NPC476716
0.77	Intermediate Similarity	NPC183571
0.7692	Intermediate Similarity	NPC65133
0.7692	Intermediate Similarity	NPC139566
0.7692	Intermediate Similarity	NPC235014
0.7684	Intermediate Similarity	NPC49420
0.7677	Intermediate Similarity	NPC470761
0.7677	Intermediate Similarity	NPC473219
0.7677	Intermediate Similarity	NPC477656
0.7647	Intermediate Similarity	NPC471333
0.7647	Intermediate Similarity	NPC471332
0.7642	Intermediate Similarity	NPC473535
0.7634	Intermediate Similarity	NPC167877
0.7634	Intermediate Similarity	NPC171722
0.7624	Intermediate Similarity	NPC36688
0.7624	Intermediate Similarity	NPC474165
0.7624	Intermediate Similarity	NPC474166
0.7624	Intermediate Similarity	NPC69171
0.7624	Intermediate Similarity	NPC159533
0.7624	Intermediate Similarity	NPC19239
0.7596	Intermediate Similarity	NPC469370
0.7593	Intermediate Similarity	NPC473656
0.7582	Intermediate Similarity	NPC22611
0.7582	Intermediate Similarity	NPC470948
0.7579	Intermediate Similarity	NPC158488
0.7579	Intermediate Similarity	NPC214292
0.7576	Intermediate Similarity	NPC216478
0.7573	Intermediate Similarity	NPC293512
0.7573	Intermediate Similarity	NPC475510
0.7573	Intermediate Similarity	NPC180744
0.7573	Intermediate Similarity	NPC475587
0.7573	Intermediate Similarity	NPC59530
0.7556	Intermediate Similarity	NPC327002
0.7556	Intermediate Similarity	NPC476988
0.7556	Intermediate Similarity	NPC474955
0.7553	Intermediate Similarity	NPC28227
0.7553	Intermediate Similarity	NPC226863
0.7553	Intermediate Similarity	NPC215831
0.7553	Intermediate Similarity	NPC474845
0.7549	Intermediate Similarity	NPC258532
0.7549	Intermediate Similarity	NPC228669
0.7549	Intermediate Similarity	NPC164835
0.7526	Intermediate Similarity	NPC470697
0.7524	Intermediate Similarity	NPC253906
0.7524	Intermediate Similarity	NPC474567
0.7523	Intermediate Similarity	NPC475372
0.7523	Intermediate Similarity	NPC106644
0.75	Intermediate Similarity	NPC477655
0.75	Intermediate Similarity	NPC469407
0.75	Intermediate Similarity	NPC94377
0.75	Intermediate Similarity	NPC473939
0.75	Intermediate Similarity	NPC477509
0.75	Intermediate Similarity	NPC474631
0.75	Intermediate Similarity	NPC167974
0.75	Intermediate Similarity	NPC473595
0.75	Intermediate Similarity	NPC270478
0.75	Intermediate Similarity	NPC258323
0.75	Intermediate Similarity	NPC97505
0.7477	Intermediate Similarity	NPC470120
0.7476	Intermediate Similarity	NPC102352
0.7475	Intermediate Similarity	NPC27105
0.7475	Intermediate Similarity	NPC124246
0.7474	Intermediate Similarity	NPC73995
0.7473	Intermediate Similarity	NPC178676
0.7455	Intermediate Similarity	NPC475520
0.7455	Intermediate Similarity	NPC312536
0.7451	Intermediate Similarity	NPC99510
0.7447	Intermediate Similarity	NPC175293
0.7444	Intermediate Similarity	NPC170038
0.7444	Intermediate Similarity	NPC474978
0.7431	Intermediate Similarity	NPC470854
0.7431	Intermediate Similarity	NPC474654
0.7431	Intermediate Similarity	NPC176513
0.7431	Intermediate Similarity	NPC287343
0.7431	Intermediate Similarity	NPC97908
0.7431	Intermediate Similarity	NPC470775
0.7431	Intermediate Similarity	NPC122033
0.7431	Intermediate Similarity	NPC469684
0.7429	Intermediate Similarity	NPC42662
0.7429	Intermediate Similarity	NPC474242
0.7429	Intermediate Similarity	NPC218853
0.7426	Intermediate Similarity	NPC476134
0.7426	Intermediate Similarity	NPC101067
0.7423	Intermediate Similarity	NPC470224
0.7419	Intermediate Similarity	NPC76333
0.7419	Intermediate Similarity	NPC52628
0.7419	Intermediate Similarity	NPC329738
0.7416	Intermediate Similarity	NPC4827
0.7416	Intermediate Similarity	NPC321514
0.7404	Intermediate Similarity	NPC112780
0.7404	Intermediate Similarity	NPC230541
0.7404	Intermediate Similarity	NPC144854
0.7404	Intermediate Similarity	NPC3316
0.74	Intermediate Similarity	NPC271387
0.74	Intermediate Similarity	NPC153792
0.74	Intermediate Similarity	NPC164349
0.74	Intermediate Similarity	NPC472687
0.74	Intermediate Similarity	NPC471331
0.74	Intermediate Similarity	NPC99657
0.74	Intermediate Similarity	NPC471330
0.74	Intermediate Similarity	NPC203388
0.74	Intermediate Similarity	NPC241657
0.74	Intermediate Similarity	NPC264378
0.7396	Intermediate Similarity	NPC212679
0.7396	Intermediate Similarity	NPC220454
0.7396	Intermediate Similarity	NPC469595
0.7396	Intermediate Similarity	NPC475776
0.7396	Intermediate Similarity	NPC152467
0.7386	Intermediate Similarity	NPC92489
0.7383	Intermediate Similarity	NPC472002
0.7379	Intermediate Similarity	NPC475036
0.7368	Intermediate Similarity	NPC250687
0.7368	Intermediate Similarity	NPC471221
0.7368	Intermediate Similarity	NPC309656
0.7368	Intermediate Similarity	NPC254572
0.7368	Intermediate Similarity	NPC221993
0.7368	Intermediate Similarity	NPC48824
0.7368	Intermediate Similarity	NPC229407
0.7364	Intermediate Similarity	NPC17772
0.7364	Intermediate Similarity	NPC470776
0.7364	Intermediate Similarity	NPC473720
0.7363	Intermediate Similarity	NPC473420
0.7363	Intermediate Similarity	NPC476101
0.7363	Intermediate Similarity	NPC207188
0.7363	Intermediate Similarity	NPC282293
0.7358	Intermediate Similarity	NPC101450
0.7358	Intermediate Similarity	NPC473594
0.7358	Intermediate Similarity	NPC473843
0.7358	Intermediate Similarity	NPC250956
0.7358	Intermediate Similarity	NPC281624
0.7358	Intermediate Similarity	NPC474586
0.7358	Intermediate Similarity	NPC5284
0.7358	Intermediate Similarity	NPC473975
0.7358	Intermediate Similarity	NPC5103
0.7358	Intermediate Similarity	NPC475463
0.7353	Intermediate Similarity	NPC273005
0.7353	Intermediate Similarity	NPC469606
0.7353	Intermediate Similarity	NPC475558
0.7353	Intermediate Similarity	NPC31058
0.7353	Intermediate Similarity	NPC58329
0.7353	Intermediate Similarity	NPC473788
0.7347	Intermediate Similarity	NPC477129
0.7347	Intermediate Similarity	NPC100257
0.7347	Intermediate Similarity	NPC224410
0.7347	Intermediate Similarity	NPC473434
0.7347	Intermediate Similarity	NPC474841
0.7347	Intermediate Similarity	NPC477130
0.7347	Intermediate Similarity	NPC471446
0.734	Intermediate Similarity	NPC264127
0.734	Intermediate Similarity	NPC244174
0.734	Intermediate Similarity	NPC471219
0.734	Intermediate Similarity	NPC262085
0.734	Intermediate Similarity	NPC214315
0.7333	Intermediate Similarity	NPC327674
0.7333	Intermediate Similarity	NPC151393
0.7333	Intermediate Similarity	NPC154608
0.7333	Intermediate Similarity	NPC118987
0.7333	Intermediate Similarity	NPC277017
0.7333	Intermediate Similarity	NPC192813
0.7327	Intermediate Similarity	NPC54705
0.732	Intermediate Similarity	NPC252433
0.732	Intermediate Similarity	NPC186363
0.732	Intermediate Similarity	NPC233345
0.732	Intermediate Similarity	NPC207641
0.732	Intermediate Similarity	NPC165180
0.732	Intermediate Similarity	NPC233437
0.7315	Intermediate Similarity	NPC194273
0.7315	Intermediate Similarity	NPC312017
0.7315	Intermediate Similarity	NPC49451
0.7315	Intermediate Similarity	NPC9848
0.7312	Intermediate Similarity	NPC312660
0.7312	Intermediate Similarity	NPC475193
0.7312	Intermediate Similarity	NPC120158
0.7308	Intermediate Similarity	NPC96377
0.7308	Intermediate Similarity	NPC477125
0.7308	Intermediate Similarity	NPC127609
0.7308	Intermediate Similarity	NPC469874

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 NPC471222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1766
0.2-0.3	4188
0.3-0.4	2049
0.4-0.5	521
0.5-0.6	316
0.6-0.7	126
0.7-0.8	12
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
0.7476	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1694	Approved
0.7216	Intermediate Similarity	NPD5207	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.7172	Intermediate Similarity	NPD6001	Approved
0.7158	Intermediate Similarity	NPD7521	Approved
0.7158	Intermediate Similarity	NPD7334	Approved
0.7158	Intermediate Similarity	NPD7146	Approved
0.7158	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD6409	Approved
0.7158	Intermediate Similarity	NPD5330	Approved
0.7075	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6399	Phase 3
0.7059	Intermediate Similarity	NPD4225	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5282	Discontinued
0.6979	Remote Similarity	NPD6098	Approved
0.697	Remote Similarity	NPD6411	Approved
0.6931	Remote Similarity	NPD5695	Phase 3
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3573	Approved
0.69	Remote Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD5779	Approved
0.6893	Remote Similarity	NPD5696	Approved
0.6881	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7492	Approved
0.6837	Remote Similarity	NPD5208	Approved
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6814	Remote Similarity	NPD7115	Discovery
0.6804	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6054	Approved
0.6783	Remote Similarity	NPD6059	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.678	Remote Similarity	NPD6616	Approved
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD6904	Approved
0.6768	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD1695	Approved
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3667	Approved
0.6724	Remote Similarity	NPD6015	Approved
0.6724	Remote Similarity	NPD6016	Approved
0.6723	Remote Similarity	NPD8293	Discontinued
0.6723	Remote Similarity	NPD7078	Approved
0.67	Remote Similarity	NPD5692	Phase 3
0.6697	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7902	Approved
0.6634	Remote Similarity	NPD5694	Approved
0.6634	Remote Similarity	NPD5693	Phase 1
0.6634	Remote Similarity	NPD6050	Approved
0.6633	Remote Similarity	NPD3618	Phase 1
0.6606	Remote Similarity	NPD6412	Phase 2
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3668	Phase 3
0.6598	Remote Similarity	NPD4786	Approved
0.6571	Remote Similarity	NPD7638	Approved
0.6549	Remote Similarity	NPD4632	Approved
0.6545	Remote Similarity	NPD7320	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6514	Remote Similarity	NPD6675	Approved
0.6514	Remote Similarity	NPD6402	Approved
0.6514	Remote Similarity	NPD5739	Approved
0.6514	Remote Similarity	NPD7128	Approved
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6486	Remote Similarity	NPD6373	Approved
0.6486	Remote Similarity	NPD6372	Approved
0.6481	Remote Similarity	NPD6052	Approved
0.6471	Remote Similarity	NPD8328	Phase 3
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD5284	Approved
0.6471	Remote Similarity	NPD7637	Suspended
0.646	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD5697	Approved
0.6455	Remote Similarity	NPD5701	Approved
0.6442	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5654	Approved
0.6436	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD3133	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6396	Remote Similarity	NPD6899	Approved
0.6392	Remote Similarity	NPD4221	Approved
0.6392	Remote Similarity	NPD4223	Phase 3
0.6379	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD6649	Approved
0.6372	Remote Similarity	NPD6650	Approved
0.6344	Remote Similarity	NPD8039	Approved
0.6341	Remote Similarity	NPD7319	Approved
0.6339	Remote Similarity	NPD6012	Approved
0.6339	Remote Similarity	NPD6013	Approved
0.6339	Remote Similarity	NPD6014	Approved
0.6321	Remote Similarity	NPD5959	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.6311	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD8035	Phase 2
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8516	Approved
0.6303	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD1700	Approved
0.6289	Remote Similarity	NPD5369	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD4634	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6275	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6051	Approved
0.6275	Remote Similarity	NPD5328	Approved
0.6263	Remote Similarity	NPD4197	Approved
0.626	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD4202	Approved
0.623	Remote Similarity	NPD7507	Approved
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD6847	Approved
0.6226	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD229	Approved
0.6214	Remote Similarity	NPD6698	Approved
0.6214	Remote Similarity	NPD46	Approved
0.62	Remote Similarity	NPD5329	Approved
0.62	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7604	Phase 2
0.6186	Remote Similarity	NPD4695	Discontinued
0.6174	Remote Similarity	NPD6882	Approved
0.6168	Remote Similarity	NPD4755	Approved
0.616	Remote Similarity	NPD5956	Approved
0.6154	Remote Similarity	NPD4137	Phase 3
0.6154	Remote Similarity	NPD6079	Approved
0.6146	Remote Similarity	NPD3617	Approved
0.6139	Remote Similarity	NPD4519	Discontinued
0.6139	Remote Similarity	NPD4694	Approved
0.6139	Remote Similarity	NPD4623	Approved
0.6139	Remote Similarity	NPD5280	Approved
0.6139	Remote Similarity	NPD4693	Phase 3
0.6139	Remote Similarity	NPD5690	Phase 2
0.6139	Remote Similarity	NPD4689	Approved
0.6139	Remote Similarity	NPD4138	Approved
0.6139	Remote Similarity	NPD4690	Approved
0.6139	Remote Similarity	NPD5279	Phase 3
0.6139	Remote Similarity	NPD4688	Approved
0.6139	Remote Similarity	NPD5205	Approved
0.6122	Remote Similarity	NPD1780	Approved
0.6122	Remote Similarity	NPD4692	Approved
0.6122	Remote Similarity	NPD1779	Approved
0.6122	Remote Similarity	NPD4139	Approved
0.6121	Remote Similarity	NPD8133	Approved
0.6098	Remote Similarity	NPD6336	Discontinued
0.6091	Remote Similarity	NPD7632	Discontinued
0.6087	Remote Similarity	NPD4691	Approved
0.6087	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4747	Approved
0.6078	Remote Similarity	NPD7524	Approved
0.6075	Remote Similarity	NPD7732	Phase 3
0.6075	Remote Similarity	NPD4697	Phase 3
0.6066	Remote Similarity	NPD6067	Discontinued
0.6055	Remote Similarity	NPD5285	Approved
0.6055	Remote Similarity	NPD5286	Approved
0.6055	Remote Similarity	NPD4700	Approved
0.6055	Remote Similarity	NPD4696	Approved
0.6048	Remote Similarity	NPD8074	Phase 3
0.6044	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6921	Approved
0.6033	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5777	Approved
0.6018	Remote Similarity	NPD6614	Approved
0.6017	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.598	Remote Similarity	NPD4249	Approved
0.5946	Remote Similarity	NPD4633	Approved
0.5946	Remote Similarity	NPD5211	Phase 2
0.5946	Remote Similarity	NPD5224	Approved
0.5946	Remote Similarity	NPD5225	Approved
0.5946	Remote Similarity	NPD5226	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