NPASS Compound

Structure

NPC475816 OpenBabel07101718302D 29 33 0 0 1 0 0 0 0 0999 V2000 -0.8371 2.7665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4813 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5345 4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7493 2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 2.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8001 -0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1321 1.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8832 0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1856 1.3570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1268 2.5005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3288 0.5679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7493 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0662 0.8831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3784 1.5326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0172 1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0172 2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4784 1.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8011 -0.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1850 2.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4794 1.7370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0662 2.5012 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 3.2022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1942 -0.9555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1645 2.2826 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6153 0.6921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1300 3.4334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 24 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 1 1 1 0 0 0 11 25 1 0 0 0 0 12 8 1 6 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 11 1 1 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.18
Volume:	396.412
LogP:	2.184
LogD:	2.084
LogS:	-3.282
# Rotatable Bonds:	4
TPSA:	91.86
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	5.406
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.514
MDCK Permeability:	7.3354863161512185e-06
Pgp-inhibitor:	0.051
Pgp-substrate:	0.762
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.526

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	83.79998016357422%
Volume Distribution (VD):	0.866
Pgp-substrate:	15.166653633117676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.647
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.839

ADMET: Excretion

Clearance (CL):	7.549
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.604
Drug-inuced Liver Injury (DILI):	0.404
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.036
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.797

Download Data

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

Natural Product: NPC475816

Natural Product ID:	NPC475816
*Common Name:**	OZUSKNIPJRUWKJ-VKGPKCIYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZUSKNIPJRUWKJ-VKGPKCIYSA-N
Standard InCHI:	InChI=1S/C22H26N2O5/c1-11(25)15-8-12-10-22(21(27)29-3)18-14(6-7-24(19(15)22)20(12)26)16-9-13(28-2)4-5-17(16)23-18/h4-5,9,11-12,15,19,23,25H,6-8,10H2,1-3H3/t11-,12+,15-,19+,22-/m1/s1
SMILES:	CC(C1CC2CC3(C1N(C2=O)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516622
PubChem CID:	44566747
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO32495	tabernaemontana calcarea	Species	Apocynaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[12713407]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6.8	ug.mL-1	PMID[486688]

☑ 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 NPC475816 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	387
0.1-0.2	1735
0.2-0.3	6941
0.3-0.4	11323
0.4-0.5	15749
0.5-0.6	3816
0.6-0.7	2246
0.7-0.8	421
0.8-0.85	57
0.85-0.9	11
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC474192
0.9716	High Similarity	NPC475720
0.939	High Similarity	NPC311906
0.9147	High Similarity	NPC96321
0.9128	High Similarity	NPC473105
0.8873	High Similarity	NPC469928
0.8726	High Similarity	NPC471304
0.8704	High Similarity	NPC473041
0.8584	High Similarity	NPC329982
0.8475	Intermediate Similarity	NPC478078
0.844	Intermediate Similarity	NPC330009
0.839	Intermediate Similarity	NPC478080
0.8355	Intermediate Similarity	NPC473540
0.8304	Intermediate Similarity	NPC21638
0.8291	Intermediate Similarity	NPC17437
0.8216	Intermediate Similarity	NPC329793
0.8182	Intermediate Similarity	NPC478074
0.8155	Intermediate Similarity	NPC477066
0.8125	Intermediate Similarity	NPC472099
0.812	Intermediate Similarity	NPC478082
0.812	Intermediate Similarity	NPC478081
0.812	Intermediate Similarity	NPC477067
0.8119	Intermediate Similarity	NPC475910
0.8108	Intermediate Similarity	NPC152768
0.8108	Intermediate Similarity	NPC148183
0.8051	Intermediate Similarity	NPC81939
0.8017	Intermediate Similarity	NPC475666
0.7973	Intermediate Similarity	NPC472098
0.7963	Intermediate Similarity	NPC329747
0.7962	Intermediate Similarity	NPC329858
0.7945	Intermediate Similarity	NPC300156
0.7915	Intermediate Similarity	NPC470784
0.7913	Intermediate Similarity	NPC157931
0.7911	Intermediate Similarity	NPC305984
0.7876	Intermediate Similarity	NPC303658
0.7872	Intermediate Similarity	NPC184680
0.7839	Intermediate Similarity	NPC470785
0.7817	Intermediate Similarity	NPC471303
0.7808	Intermediate Similarity	NPC162730
0.7793	Intermediate Similarity	NPC314333
0.7783	Intermediate Similarity	NPC472111
0.7783	Intermediate Similarity	NPC45190
0.7773	Intermediate Similarity	NPC476098
0.7754	Intermediate Similarity	NPC477549
0.7748	Intermediate Similarity	NPC53344
0.7733	Intermediate Similarity	NPC191489
0.7733	Intermediate Similarity	NPC475778
0.7731	Intermediate Similarity	NPC276517
0.7727	Intermediate Similarity	NPC474116
0.7727	Intermediate Similarity	NPC474077
0.7725	Intermediate Similarity	NPC194740
0.7723	Intermediate Similarity	NPC234999
0.7717	Intermediate Similarity	NPC199851
0.7717	Intermediate Similarity	NPC312870
0.7717	Intermediate Similarity	NPC294909
0.7717	Intermediate Similarity	NPC128265
0.7717	Intermediate Similarity	NPC254240
0.7704	Intermediate Similarity	NPC260909
0.7702	Intermediate Similarity	NPC54803
0.7702	Intermediate Similarity	NPC321592
0.7696	Intermediate Similarity	NPC280799
0.7692	Intermediate Similarity	NPC223409
0.7689	Intermediate Similarity	NPC87413
0.7686	Intermediate Similarity	NPC74360
0.7683	Intermediate Similarity	NPC478083
0.7682	Intermediate Similarity	NPC261251
0.768	Intermediate Similarity	NPC88923
0.768	Intermediate Similarity	NPC315634
0.768	Intermediate Similarity	NPC100734
0.7671	Intermediate Similarity	NPC241024
0.7668	Intermediate Similarity	NPC321428
0.7668	Intermediate Similarity	NPC270918
0.765	Intermediate Similarity	NPC100547
0.7642	Intermediate Similarity	NPC469594
0.7639	Intermediate Similarity	NPC214142
0.7639	Intermediate Similarity	NPC319232
0.7639	Intermediate Similarity	NPC55493
0.7639	Intermediate Similarity	NPC24370
0.7636	Intermediate Similarity	NPC249040
0.7633	Intermediate Similarity	NPC189079
0.7625	Intermediate Similarity	NPC475844
0.7621	Intermediate Similarity	NPC284685
0.7619	Intermediate Similarity	NPC60621
0.7617	Intermediate Similarity	NPC95240
0.7617	Intermediate Similarity	NPC195788
0.7617	Intermediate Similarity	NPC237901
0.7617	Intermediate Similarity	NPC322135
0.7607	Intermediate Similarity	NPC304307
0.7607	Intermediate Similarity	NPC118559
0.7607	Intermediate Similarity	NPC34580
0.7607	Intermediate Similarity	NPC124920
0.7592	Intermediate Similarity	NPC133609
0.7589	Intermediate Similarity	NPC4687
0.7585	Intermediate Similarity	NPC474688
0.7585	Intermediate Similarity	NPC14288
0.7574	Intermediate Similarity	NPC66777
0.7574	Intermediate Similarity	NPC33949
0.7574	Intermediate Similarity	NPC471762
0.7571	Intermediate Similarity	NPC303374
0.7565	Intermediate Similarity	NPC184408
0.7545	Intermediate Similarity	NPC277350
0.7544	Intermediate Similarity	NPC469592
0.7544	Intermediate Similarity	NPC471080
0.7542	Intermediate Similarity	NPC82472
0.7534	Intermediate Similarity	NPC223427
0.7534	Intermediate Similarity	NPC251090
0.7522	Intermediate Similarity	NPC469743
0.7521	Intermediate Similarity	NPC284888
0.752	Intermediate Similarity	NPC473800
0.7512	Intermediate Similarity	NPC176127
0.7511	Intermediate Similarity	NPC88008
0.7511	Intermediate Similarity	NPC193238
0.75	Intermediate Similarity	NPC174760
0.7489	Intermediate Similarity	NPC46561
0.7478	Intermediate Similarity	NPC39679
0.7478	Intermediate Similarity	NPC74969
0.7477	Intermediate Similarity	NPC195461
0.7477	Intermediate Similarity	NPC79129
0.7477	Intermediate Similarity	NPC81654
0.7477	Intermediate Similarity	NPC249150
0.7477	Intermediate Similarity	NPC213308
0.7477	Intermediate Similarity	NPC313985
0.7477	Intermediate Similarity	NPC49196
0.7467	Intermediate Similarity	NPC39500
0.7467	Intermediate Similarity	NPC475841
0.7467	Intermediate Similarity	NPC474145
0.7466	Intermediate Similarity	NPC52557
0.7458	Intermediate Similarity	NPC257851
0.7448	Intermediate Similarity	NPC323752
0.7448	Intermediate Similarity	NPC323198
0.7447	Intermediate Similarity	NPC473449
0.7446	Intermediate Similarity	NPC169402
0.7443	Intermediate Similarity	NPC307963
0.7437	Intermediate Similarity	NPC474701
0.7436	Intermediate Similarity	NPC280272
0.7434	Intermediate Similarity	NPC249583
0.7432	Intermediate Similarity	NPC280714
0.7426	Intermediate Similarity	NPC274640
0.7425	Intermediate Similarity	NPC323969
0.7425	Intermediate Similarity	NPC150239
0.7424	Intermediate Similarity	NPC264176
0.7419	Intermediate Similarity	NPC102338
0.7419	Intermediate Similarity	NPC63199
0.7419	Intermediate Similarity	NPC196251
0.7419	Intermediate Similarity	NPC111602
0.7417	Intermediate Similarity	NPC33064
0.7417	Intermediate Similarity	NPC245055
0.7417	Intermediate Similarity	NPC39370
0.7414	Intermediate Similarity	NPC82070
0.7406	Intermediate Similarity	NPC473186
0.7399	Intermediate Similarity	NPC315491
0.7399	Intermediate Similarity	NPC45459
0.7397	Intermediate Similarity	NPC474183
0.7393	Intermediate Similarity	NPC329688
0.7393	Intermediate Similarity	NPC189812
0.7391	Intermediate Similarity	NPC316181
0.7391	Intermediate Similarity	NPC151781
0.7391	Intermediate Similarity	NPC74562
0.7389	Intermediate Similarity	NPC195787
0.7389	Intermediate Similarity	NPC246140
0.7387	Intermediate Similarity	NPC306376
0.7387	Intermediate Similarity	NPC50503
0.7382	Intermediate Similarity	NPC52254
0.738	Intermediate Similarity	NPC9894
0.738	Intermediate Similarity	NPC208284
0.7364	Intermediate Similarity	NPC203972
0.7362	Intermediate Similarity	NPC144452
0.7359	Intermediate Similarity	NPC118228
0.7359	Intermediate Similarity	NPC116238
0.7357	Intermediate Similarity	NPC193777
0.7355	Intermediate Similarity	NPC15801
0.7355	Intermediate Similarity	NPC6786
0.7352	Intermediate Similarity	NPC92111
0.735	Intermediate Similarity	NPC132642
0.735	Intermediate Similarity	NPC128115
0.7345	Intermediate Similarity	NPC87714
0.7345	Intermediate Similarity	NPC165349
0.7345	Intermediate Similarity	NPC329708
0.7345	Intermediate Similarity	NPC264166
0.7345	Intermediate Similarity	NPC274291
0.7345	Intermediate Similarity	NPC47059
0.7345	Intermediate Similarity	NPC118832
0.7339	Intermediate Similarity	NPC175474
0.7339	Intermediate Similarity	NPC174788
0.7339	Intermediate Similarity	NPC247803
0.7331	Intermediate Similarity	NPC475271
0.733	Intermediate Similarity	NPC131017
0.7325	Intermediate Similarity	NPC131486
0.7321	Intermediate Similarity	NPC214428
0.732	Intermediate Similarity	NPC244543
0.7316	Intermediate Similarity	NPC472291
0.7309	Intermediate Similarity	NPC67401
0.7308	Intermediate Similarity	NPC288987
0.7306	Intermediate Similarity	NPC76748
0.7304	Intermediate Similarity	NPC187501
0.7301	Intermediate Similarity	NPC162484
0.73	Intermediate Similarity	NPC179287
0.7293	Intermediate Similarity	NPC476116
0.7284	Intermediate Similarity	NPC184225
0.7277	Intermediate Similarity	NPC128823

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 NPC475816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	563
0.2-0.3	723
0.3-0.4	1588
0.4-0.5	2720
0.5-0.6	2358
0.6-0.7	844
0.7-0.8	141
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8341	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD8358	Approved
0.7895	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD4885	Approved
0.78	Intermediate Similarity	NPD8363	Approved
0.78	Intermediate Similarity	NPD8364	Approved
0.7793	Intermediate Similarity	NPD4499	Approved
0.7738	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7708	Approved
0.7731	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD8016	Phase 3
0.7717	Intermediate Similarity	NPD4501	Approved
0.7717	Intermediate Similarity	NPD4500	Approved
0.7704	Intermediate Similarity	NPD8460	Approved
0.7704	Intermediate Similarity	NPD8459	Approved
0.768	Intermediate Similarity	NPD7803	Approved
0.7673	Intermediate Similarity	NPD8463	Approved
0.7621	Intermediate Similarity	NPD7955	Approved
0.7621	Intermediate Similarity	NPD7956	Approved
0.7617	Intermediate Similarity	NPD8466	Approved
0.7617	Intermediate Similarity	NPD8465	Approved
0.7617	Intermediate Similarity	NPD8467	Approved
0.7609	Intermediate Similarity	NPD3258	Approved
0.7603	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6517	Phase 3
0.7586	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5658	Approved
0.7542	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3006	Discontinued
0.7521	Intermediate Similarity	NPD4373	Phase 2
0.75	Intermediate Similarity	NPD8425	Approved
0.75	Intermediate Similarity	NPD6242	Discontinued
0.75	Intermediate Similarity	NPD8426	Approved
0.7481	Intermediate Similarity	NPD8428	Approved
0.7481	Intermediate Similarity	NPD8429	Approved
0.7481	Intermediate Similarity	NPD8427	Approved
0.7478	Intermediate Similarity	NPD6376	Discontinued
0.7478	Intermediate Similarity	NPD2916	Discontinued
0.7477	Intermediate Similarity	NPD4601	Approved
0.7477	Intermediate Similarity	NPD4600	Approved
0.7469	Intermediate Similarity	NPD6276	Discontinued
0.7468	Intermediate Similarity	NPD4952	Phase 3
0.7456	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6716	Phase 1
0.7443	Intermediate Similarity	NPD1038	Approved
0.7439	Intermediate Similarity	NPD8102	Discontinued
0.7435	Intermediate Similarity	NPD3257	Approved
0.7435	Intermediate Similarity	NPD4897	Phase 2
0.7435	Intermediate Similarity	NPD5293	Phase 2
0.7414	Intermediate Similarity	NPD5632	Approved
0.7409	Intermediate Similarity	NPD4418	Discontinued
0.7409	Intermediate Similarity	NPD5482	Discontinued
0.7406	Intermediate Similarity	NPD7797	Approved
0.7406	Intermediate Similarity	NPD7796	Approved
0.7399	Intermediate Similarity	NPD484	Approved
0.7389	Intermediate Similarity	NPD3003	Approved
0.7384	Intermediate Similarity	NPD4328	Approved
0.7382	Intermediate Similarity	NPD6770	Approved
0.738	Intermediate Similarity	NPD7470	Discontinued
0.7371	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7453	Approved
0.7357	Intermediate Similarity	NPD7452	Approved
0.7353	Intermediate Similarity	NPD5014	Discontinued
0.7353	Intermediate Similarity	NPD5559	Phase 2
0.7345	Intermediate Similarity	NPD4039	Approved
0.7345	Intermediate Similarity	NPD4036	Approved
0.7345	Intermediate Similarity	NPD4034	Approved
0.7345	Intermediate Similarity	NPD31	Approved
0.7345	Intermediate Similarity	NPD4038	Approved
0.7345	Intermediate Similarity	NPD4037	Approved
0.7345	Intermediate Similarity	NPD4122	Approved
0.7345	Intermediate Similarity	NPD4033	Approved
0.7345	Intermediate Similarity	NPD32	Approved
0.7345	Intermediate Similarity	NPD4035	Approved
0.7342	Intermediate Similarity	NPD5003	Discontinued
0.7339	Intermediate Similarity	NPD7878	Phase 2
0.7339	Intermediate Similarity	NPD3354	Phase 2
0.733	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4502	Phase 2
0.7304	Intermediate Similarity	NPD5416	Discontinued
0.7302	Intermediate Similarity	NPD8091	Phase 3
0.7301	Intermediate Similarity	NPD6176	Phase 1
0.7297	Intermediate Similarity	NPD5512	Phase 3
0.7295	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4506	Discontinued
0.7285	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7222	Phase 2
0.728	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7417	Discontinued
0.7253	Intermediate Similarity	NPD5612	Discontinued
0.7246	Intermediate Similarity	NPD5507	Approved
0.7246	Intermediate Similarity	NPD5506	Approved
0.724	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4558	Phase 2
0.7224	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5488	Discontinued
0.7218	Intermediate Similarity	NPD8359	Phase 2
0.721	Intermediate Similarity	NPD5903	Approved
0.721	Intermediate Similarity	NPD5902	Approved
0.721	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5429	Discontinued
0.7202	Intermediate Similarity	NPD6963	Approved
0.7202	Intermediate Similarity	NPD6964	Approved
0.72	Intermediate Similarity	NPD1768	Approved
0.7198	Intermediate Similarity	NPD7069	Discontinued
0.7197	Intermediate Similarity	NPD7603	Discontinued
0.7196	Intermediate Similarity	NPD8489	Phase 1
0.7195	Intermediate Similarity	NPD6790	Phase 1
0.7194	Intermediate Similarity	NPD8255	Phase 2
0.7191	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7194	Discontinued
0.716	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7777	Approved
0.7156	Intermediate Similarity	NPD53	Approved
0.7156	Intermediate Similarity	NPD7778	Approved
0.7155	Intermediate Similarity	NPD6220	Phase 3
0.7143	Intermediate Similarity	NPD6995	Phase 1
0.7132	Intermediate Similarity	NPD5450	Discontinued
0.7131	Intermediate Similarity	NPD8101	Phase 3
0.7125	Intermediate Similarity	NPD7426	Phase 1
0.7125	Intermediate Similarity	NPD3263	Phase 3
0.7109	Intermediate Similarity	NPD6530	Approved
0.7109	Intermediate Similarity	NPD6531	Approved
0.7102	Intermediate Similarity	NPD7853	Phase 2
0.71	Intermediate Similarity	NPD2509	Approved
0.71	Intermediate Similarity	NPD2510	Approved
0.7095	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7558	Phase 2
0.7087	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6962	Phase 2
0.7073	Intermediate Similarity	NPD5805	Approved
0.7072	Intermediate Similarity	NPD2564	Approved
0.7072	Intermediate Similarity	NPD2565	Phase 2
0.7067	Intermediate Similarity	NPD6550	Discontinued
0.7064	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7395	Discontinued
0.7046	Intermediate Similarity	NPD4429	Discontinued
0.7046	Intermediate Similarity	NPD6985	Discontinued
0.7043	Intermediate Similarity	NPD5901	Discontinued
0.7043	Intermediate Similarity	NPD3947	Discontinued
0.7037	Intermediate Similarity	NPD5022	Discontinued
0.7034	Intermediate Similarity	NPD3393	Approved
0.7034	Intermediate Similarity	NPD3394	Approved
0.7034	Intermediate Similarity	NPD3389	Approved
0.7031	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5530	Phase 1
0.7013	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8100	Phase 3
0.7008	Intermediate Similarity	NPD7859	Phase 2
0.7004	Intermediate Similarity	NPD4368	Phase 2
0.7	Intermediate Similarity	NPD6209	Approved
0.6987	Remote Similarity	NPD5930	Phase 3
0.6986	Remote Similarity	NPD4204	Approved
0.6986	Remote Similarity	NPD4203	Approved
0.6983	Remote Similarity	NPD1392	Approved
0.6971	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4795	Phase 2
0.6964	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7994	Phase 2
0.6955	Remote Similarity	NPD3259	Approved
0.6955	Remote Similarity	NPD4845	Discontinued
0.6951	Remote Similarity	NPD6494	Phase 2
0.6949	Remote Similarity	NPD3243	Approved
0.6942	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7688	Phase 1
0.6933	Remote Similarity	NPD5164	Discontinued
0.6926	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7548	Discontinued
0.69	Remote Similarity	NPD2175	Phase 3
0.69	Remote Similarity	NPD3825	Phase 3
0.69	Remote Similarity	NPD2177	Approved
0.69	Remote Similarity	NPD2176	Approved
0.6898	Remote Similarity	NPD5479	Discontinued
0.6897	Remote Similarity	NPD5426	Phase 3
0.6892	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2844	Phase 3
0.688	Remote Similarity	NPD2187	Approved
0.688	Remote Similarity	NPD2189	Approved
0.688	Remote Similarity	NPD4154	Approved
0.6878	Remote Similarity	NPD2092	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