NPASS Compound

Structure

NPC475720 OpenBabel07101718222D 28 32 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 0.8011 -0.0360 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 -0.1850 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 3 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 -1.1645 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 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 24 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 1 1 1 0 0 0 12 25 1 0 0 0 0 13 8 1 6 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 12 1 1 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 6 0 0 0 20 24 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.2
Volume:	390.258
LogP:	2.761
LogD:	2.651
LogS:	-2.744
# Rotatable Bonds:	4
TPSA:	74.79
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.794
Synthetic Accessibility Score:	5.219
Fsp3:	0.591
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:	-5.508
MDCK Permeability:	1.0699198355723638e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.096
20% Bioavailability (F20%):	0.18
30% Bioavailability (F30%):	0.573

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	74.71005249023438%
Volume Distribution (VD):	1.838
Pgp-substrate:	21.420730590820312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.719
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.849
CYP2D6-inhibitor:	0.919
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	10.204
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.609
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.038
Carcinogencity:	0.501
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC475720

Natural Product ID:	NPC475720
*Common Name:**	19(R)-Heyneanine
IUPAC Name:	n.a.
Synonyms:	19(R)-Heyneanine
Standard InCHIKey:	OYMQKBZMKFJPMH-WRGQPFOFSA-N
Standard InCHI:	InChI=1S/C22H28N2O4/c1-12(25)16-8-13-10-22(21(26)28-3)19-15(6-7-24(11-13)20(16)22)17-9-14(27-2)4-5-18(17)23-19/h4-5,9,12-13,16,20,23,25H,6-8,10-11H2,1-3H3/t12-,13+,16-,20+,22-/m1/s1
SMILES:	CC(C1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512646
PubChem CID:	44566753
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]
NPO31010	Ervatamia hainanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20850311]
NPO31010	Ervatamia hainanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	4.0	ug.mL-1	PMID[482630]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	730000.0	nM	PMID[482631]

☑ 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 NPC475720 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	343
0.1-0.2	1644
0.2-0.3	6199
0.3-0.4	11634
0.4-0.5	15556
0.5-0.6	4462
0.6-0.7	2253
0.7-0.8	514
0.8-0.85	57
0.85-0.9	23
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474192
0.9716	High Similarity	NPC475816
0.9415	High Similarity	NPC96321
0.9387	High Similarity	NPC473105
0.913	High Similarity	NPC469928
0.9108	High Similarity	NPC311906
0.8981	High Similarity	NPC471304
0.8952	High Similarity	NPC473041
0.8728	High Similarity	NPC329982
0.8679	High Similarity	NPC330009
0.8624	High Similarity	NPC478078
0.8609	High Similarity	NPC478080
0.8578	High Similarity	NPC473540
0.8509	High Similarity	NPC17437
0.8454	Intermediate Similarity	NPC329793
0.8447	Intermediate Similarity	NPC21638
0.8411	Intermediate Similarity	NPC478074
0.837	Intermediate Similarity	NPC477066
0.8349	Intermediate Similarity	NPC475910
0.8333	Intermediate Similarity	NPC477067
0.8333	Intermediate Similarity	NPC478082
0.8333	Intermediate Similarity	NPC478081
0.8265	Intermediate Similarity	NPC472099
0.8261	Intermediate Similarity	NPC81939
0.8249	Intermediate Similarity	NPC148183
0.8249	Intermediate Similarity	NPC152768
0.8225	Intermediate Similarity	NPC475666
0.8195	Intermediate Similarity	NPC329858
0.819	Intermediate Similarity	NPC329747
0.8111	Intermediate Similarity	NPC472098
0.8084	Intermediate Similarity	NPC300156
0.8019	Intermediate Similarity	NPC314333
0.8008	Intermediate Similarity	NPC471303
0.8	Intermediate Similarity	NPC472111
0.7952	Intermediate Similarity	NPC276517
0.7945	Intermediate Similarity	NPC475778
0.7944	Intermediate Similarity	NPC162730
0.7944	Intermediate Similarity	NPC474077
0.7936	Intermediate Similarity	NPC234999
0.7917	Intermediate Similarity	NPC45190
0.7907	Intermediate Similarity	NPC476098
0.7892	Intermediate Similarity	NPC74360
0.7887	Intermediate Similarity	NPC241024
0.788	Intermediate Similarity	NPC53344
0.7875	Intermediate Similarity	NPC478083
0.786	Intermediate Similarity	NPC474116
0.7857	Intermediate Similarity	NPC55493
0.7851	Intermediate Similarity	NPC191489
0.785	Intermediate Similarity	NPC128265
0.785	Intermediate Similarity	NPC294909
0.785	Intermediate Similarity	NPC249040
0.785	Intermediate Similarity	NPC254240
0.785	Intermediate Similarity	NPC312870
0.785	Intermediate Similarity	NPC199851
0.7848	Intermediate Similarity	NPC469594
0.7822	Intermediate Similarity	NPC280799
0.7818	Intermediate Similarity	NPC87413
0.7807	Intermediate Similarity	NPC157931
0.7798	Intermediate Similarity	NPC321428
0.7796	Intermediate Similarity	NPC315634
0.7796	Intermediate Similarity	NPC88923
0.7796	Intermediate Similarity	NPC100734
0.7748	Intermediate Similarity	NPC469592
0.7748	Intermediate Similarity	NPC471080
0.7746	Intermediate Similarity	NPC251090
0.7745	Intermediate Similarity	NPC475844
0.7743	Intermediate Similarity	NPC60621
0.7742	Intermediate Similarity	NPC223427
0.7737	Intermediate Similarity	NPC284685
0.7735	Intermediate Similarity	NPC470784
0.7729	Intermediate Similarity	NPC237901
0.7729	Intermediate Similarity	NPC176127
0.7729	Intermediate Similarity	NPC195788
0.7723	Intermediate Similarity	NPC305984
0.7717	Intermediate Similarity	NPC88008
0.7717	Intermediate Similarity	NPC4687
0.7717	Intermediate Similarity	NPC193238
0.7706	Intermediate Similarity	NPC474688
0.7696	Intermediate Similarity	NPC33949
0.7692	Intermediate Similarity	NPC184680
0.7689	Intermediate Similarity	NPC184408
0.7689	Intermediate Similarity	NPC303658
0.7679	Intermediate Similarity	NPC74969
0.7671	Intermediate Similarity	NPC475841
0.7671	Intermediate Similarity	NPC474145
0.766	Intermediate Similarity	NPC470785
0.7653	Intermediate Similarity	NPC307963
0.765	Intermediate Similarity	NPC477549
0.7647	Intermediate Similarity	NPC469743
0.7639	Intermediate Similarity	NPC280714
0.7635	Intermediate Similarity	NPC473800
0.7632	Intermediate Similarity	NPC280272
0.7621	Intermediate Similarity	NPC174760
0.7611	Intermediate Similarity	NPC46561
0.761	Intermediate Similarity	NPC329688
0.761	Intermediate Similarity	NPC189812
0.7608	Intermediate Similarity	NPC260909
0.7604	Intermediate Similarity	NPC213308
0.7604	Intermediate Similarity	NPC49196
0.7604	Intermediate Similarity	NPC79129
0.7604	Intermediate Similarity	NPC195461
0.7604	Intermediate Similarity	NPC313985
0.7604	Intermediate Similarity	NPC45459
0.7604	Intermediate Similarity	NPC315491
0.7604	Intermediate Similarity	NPC81654
0.7604	Intermediate Similarity	NPC249150
0.7602	Intermediate Similarity	NPC39679
0.7597	Intermediate Similarity	NPC321592
0.7597	Intermediate Similarity	NPC54803
0.7593	Intermediate Similarity	NPC52557
0.7589	Intermediate Similarity	NPC39500
0.7586	Intermediate Similarity	NPC223409
0.7578	Intermediate Similarity	NPC208284
0.7576	Intermediate Similarity	NPC261251
0.757	Intermediate Similarity	NPC203972
0.7566	Intermediate Similarity	NPC169402
0.7559	Intermediate Similarity	NPC92111
0.7557	Intermediate Similarity	NPC193777
0.7557	Intermediate Similarity	NPC249583
0.7554	Intermediate Similarity	NPC474701
0.7547	Intermediate Similarity	NPC63199
0.7547	Intermediate Similarity	NPC102338
0.7547	Intermediate Similarity	NPC111602
0.7547	Intermediate Similarity	NPC196251
0.7545	Intermediate Similarity	NPC118832
0.7545	Intermediate Similarity	NPC264176
0.7545	Intermediate Similarity	NPC165349
0.7545	Intermediate Similarity	NPC47059
0.7545	Intermediate Similarity	NPC274291
0.7545	Intermediate Similarity	NPC264166
0.7545	Intermediate Similarity	NPC329708
0.7544	Intermediate Similarity	NPC150239
0.7544	Intermediate Similarity	NPC132642
0.7543	Intermediate Similarity	NPC194740
0.7543	Intermediate Similarity	NPC100547
0.7543	Intermediate Similarity	NPC274640
0.7535	Intermediate Similarity	NPC131017
0.7533	Intermediate Similarity	NPC82070
0.7532	Intermediate Similarity	NPC39370
0.7532	Intermediate Similarity	NPC24370
0.7532	Intermediate Similarity	NPC319232
0.7532	Intermediate Similarity	NPC214142
0.7523	Intermediate Similarity	NPC214428
0.7521	Intermediate Similarity	NPC473186
0.7512	Intermediate Similarity	NPC306376
0.7512	Intermediate Similarity	NPC50503
0.7512	Intermediate Similarity	NPC76748
0.7511	Intermediate Similarity	NPC322135
0.7511	Intermediate Similarity	NPC195787
0.7511	Intermediate Similarity	NPC246140
0.7511	Intermediate Similarity	NPC277350
0.7511	Intermediate Similarity	NPC95240
0.75	Intermediate Similarity	NPC162484
0.75	Intermediate Similarity	NPC124920
0.75	Intermediate Similarity	NPC304307
0.75	Intermediate Similarity	NPC118559
0.75	Intermediate Similarity	NPC52254
0.75	Intermediate Similarity	NPC9894
0.75	Intermediate Similarity	NPC34580
0.7489	Intermediate Similarity	NPC476116
0.7479	Intermediate Similarity	NPC14288
0.7478	Intermediate Similarity	NPC144452
0.7478	Intermediate Similarity	NPC118228
0.7478	Intermediate Similarity	NPC116238
0.7477	Intermediate Similarity	NPC270918
0.7477	Intermediate Similarity	NPC128823
0.7476	Intermediate Similarity	NPC19679
0.7469	Intermediate Similarity	NPC303374
0.7468	Intermediate Similarity	NPC6786
0.7468	Intermediate Similarity	NPC471762
0.7468	Intermediate Similarity	NPC15801
0.7468	Intermediate Similarity	NPC66777
0.7466	Intermediate Similarity	NPC87714
0.7465	Intermediate Similarity	NPC156704
0.7465	Intermediate Similarity	NPC296527
0.7465	Intermediate Similarity	NPC70956
0.7465	Intermediate Similarity	NPC243834
0.7465	Intermediate Similarity	NPC175474
0.7459	Intermediate Similarity	NPC189079
0.7456	Intermediate Similarity	NPC247803
0.7449	Intermediate Similarity	NPC216369
0.7448	Intermediate Similarity	NPC81175
0.7448	Intermediate Similarity	NPC148889
0.7446	Intermediate Similarity	NPC475271
0.7443	Intermediate Similarity	NPC176538
0.7437	Intermediate Similarity	NPC82472
0.7434	Intermediate Similarity	NPC266931
0.7432	Intermediate Similarity	NPC476106
0.7426	Intermediate Similarity	NPC473187
0.7422	Intermediate Similarity	NPC187501
0.7418	Intermediate Similarity	NPC133609
0.7415	Intermediate Similarity	NPC284888
0.7414	Intermediate Similarity	NPC179287
0.7389	Intermediate Similarity	NPC94157
0.7389	Intermediate Similarity	NPC310211
0.7389	Intermediate Similarity	NPC219087
0.7389	Intermediate Similarity	NPC48353
0.7389	Intermediate Similarity	NPC308137
0.7387	Intermediate Similarity	NPC185742
0.7387	Intermediate Similarity	NPC475070

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 NPC475720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	562
0.2-0.3	656
0.3-0.4	1583
0.4-0.5	2594
0.5-0.6	2489
0.6-0.7	910
0.7-0.8	149
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8585	High Similarity	NPD4118	Clinical (unspecified phase)
0.8509	High Similarity	NPD8358	Approved
0.8019	Intermediate Similarity	NPD4499	Approved
0.7992	Intermediate Similarity	NPD8363	Approved
0.7992	Intermediate Similarity	NPD8364	Approved
0.7927	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7708	Approved
0.785	Intermediate Similarity	NPD4500	Approved
0.785	Intermediate Similarity	NPD4501	Approved
0.7796	Intermediate Similarity	NPD7803	Approved
0.7788	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD5658	Approved
0.7737	Intermediate Similarity	NPD7956	Approved
0.7737	Intermediate Similarity	NPD7955	Approved
0.7729	Intermediate Similarity	NPD8466	Approved
0.7729	Intermediate Similarity	NPD8467	Approved
0.7729	Intermediate Similarity	NPD8465	Approved
0.7725	Intermediate Similarity	NPD3006	Discontinued
0.7722	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6242	Discontinued
0.7672	Intermediate Similarity	NPD4885	Approved
0.7657	Intermediate Similarity	NPD6276	Discontinued
0.7653	Intermediate Similarity	NPD1038	Approved
0.7627	Intermediate Similarity	NPD8016	Phase 3
0.7627	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD4418	Discontinued
0.7611	Intermediate Similarity	NPD5632	Approved
0.7608	Intermediate Similarity	NPD8426	Approved
0.7608	Intermediate Similarity	NPD8425	Approved
0.7608	Intermediate Similarity	NPD8460	Approved
0.7608	Intermediate Similarity	NPD8459	Approved
0.7604	Intermediate Similarity	NPD4600	Approved
0.7604	Intermediate Similarity	NPD4601	Approved
0.7604	Intermediate Similarity	NPD484	Approved
0.7591	Intermediate Similarity	NPD3003	Approved
0.7589	Intermediate Similarity	NPD8428	Approved
0.7589	Intermediate Similarity	NPD8427	Approved
0.7589	Intermediate Similarity	NPD8429	Approved
0.7563	Intermediate Similarity	NPD6517	Phase 3
0.7557	Intermediate Similarity	NPD7453	Approved
0.7557	Intermediate Similarity	NPD7452	Approved
0.7546	Intermediate Similarity	NPD5003	Discontinued
0.7545	Intermediate Similarity	NPD4035	Approved
0.7545	Intermediate Similarity	NPD4037	Approved
0.7545	Intermediate Similarity	NPD4033	Approved
0.7545	Intermediate Similarity	NPD4039	Approved
0.7545	Intermediate Similarity	NPD32	Approved
0.7545	Intermediate Similarity	NPD4034	Approved
0.7545	Intermediate Similarity	NPD31	Approved
0.7545	Intermediate Similarity	NPD4038	Approved
0.7545	Intermediate Similarity	NPD4036	Approved
0.7545	Intermediate Similarity	NPD4122	Approved
0.7535	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3354	Phase 2
0.7521	Intermediate Similarity	NPD5482	Discontinued
0.7512	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3258	Approved
0.75	Intermediate Similarity	NPD5416	Discontinued
0.75	Intermediate Similarity	NPD4502	Phase 2
0.75	Intermediate Similarity	NPD5512	Phase 3
0.7489	Intermediate Similarity	NPD4373	Phase 2
0.7488	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7222	Phase 2
0.7448	Intermediate Similarity	NPD7417	Discontinued
0.7445	Intermediate Similarity	NPD5612	Discontinued
0.7436	Intermediate Similarity	NPD4952	Phase 3
0.7436	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8463	Approved
0.7424	Intermediate Similarity	NPD6770	Approved
0.7418	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5903	Approved
0.7401	Intermediate Similarity	NPD5902	Approved
0.7401	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5429	Discontinued
0.7397	Intermediate Similarity	NPD1768	Approved
0.7389	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7069	Discontinued
0.7366	Intermediate Similarity	NPD2916	Discontinued
0.7352	Intermediate Similarity	NPD53	Approved
0.7352	Intermediate Similarity	NPD7777	Approved
0.7352	Intermediate Similarity	NPD7778	Approved
0.7348	Intermediate Similarity	NPD7194	Discontinued
0.7345	Intermediate Similarity	NPD7470	Discontinued
0.7345	Intermediate Similarity	NPD6220	Phase 3
0.7344	Intermediate Similarity	NPD6716	Phase 1
0.7336	Intermediate Similarity	NPD8102	Discontinued
0.7333	Intermediate Similarity	NPD4506	Discontinued
0.7325	Intermediate Similarity	NPD4897	Phase 2
0.7325	Intermediate Similarity	NPD5488	Discontinued
0.7325	Intermediate Similarity	NPD3257	Approved
0.7325	Intermediate Similarity	NPD5293	Phase 2
0.7306	Intermediate Similarity	NPD8101	Phase 3
0.7304	Intermediate Similarity	NPD7878	Phase 2
0.73	Intermediate Similarity	NPD7797	Approved
0.73	Intermediate Similarity	NPD7796	Approved
0.7293	Intermediate Similarity	NPD8489	Phase 1
0.7289	Intermediate Similarity	NPD2510	Approved
0.7289	Intermediate Similarity	NPD6376	Discontinued
0.7289	Intermediate Similarity	NPD2509	Approved
0.7288	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4328	Approved
0.7277	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7558	Phase 2
0.7269	Intermediate Similarity	NPD8091	Phase 3
0.7269	Intermediate Similarity	NPD2565	Phase 2
0.7269	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD2564	Approved
0.7261	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6550	Discontinued
0.7257	Intermediate Similarity	NPD6962	Phase 2
0.7249	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5559	Phase 2
0.7246	Intermediate Similarity	NPD5014	Discontinued
0.7233	Intermediate Similarity	NPD5450	Discontinued
0.7232	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7395	Discontinued
0.7229	Intermediate Similarity	NPD6985	Discontinued
0.7224	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3394	Approved
0.7217	Intermediate Similarity	NPD3389	Approved
0.7217	Intermediate Similarity	NPD3393	Approved
0.7211	Intermediate Similarity	NPD6530	Approved
0.7211	Intermediate Similarity	NPD6531	Approved
0.7207	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5530	Phase 1
0.7197	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6176	Phase 1
0.7184	Intermediate Similarity	NPD8100	Phase 3
0.7183	Intermediate Similarity	NPD4203	Approved
0.7183	Intermediate Similarity	NPD4204	Approved
0.7178	Intermediate Similarity	NPD5805	Approved
0.7173	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1392	Approved
0.7167	Intermediate Similarity	NPD6964	Approved
0.7167	Intermediate Similarity	NPD6963	Approved
0.7167	Intermediate Similarity	NPD5930	Phase 3
0.7156	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4795	Phase 2
0.7156	Intermediate Similarity	NPD5901	Discontinued
0.7155	Intermediate Similarity	NPD4429	Discontinued
0.7149	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5022	Discontinued
0.7137	Intermediate Similarity	NPD5507	Approved
0.7137	Intermediate Similarity	NPD5506	Approved
0.7131	Intermediate Similarity	NPD3259	Approved
0.7131	Intermediate Similarity	NPD7994	Phase 2
0.7125	Intermediate Similarity	NPD6494	Phase 2
0.7119	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8359	Phase 2
0.7113	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5164	Discontinued
0.7111	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8255	Phase 2
0.7089	Intermediate Similarity	NPD7603	Discontinued
0.7085	Intermediate Similarity	NPD2176	Approved
0.7085	Intermediate Similarity	NPD3825	Phase 3
0.7085	Intermediate Similarity	NPD2177	Approved
0.7085	Intermediate Similarity	NPD2175	Phase 3
0.7083	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7548	Discontinued
0.7074	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2092	Phase 2
0.707	Intermediate Similarity	NPD2095	Phase 2
0.707	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2094	Phase 2
0.7066	Intermediate Similarity	NPD7853	Phase 2
0.7061	Intermediate Similarity	NPD2187	Approved
0.7061	Intermediate Similarity	NPD2189	Approved
0.7056	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4558	Phase 2
0.7054	Intermediate Similarity	NPD1740	Approved
0.7054	Intermediate Similarity	NPD1739	Approved
0.7054	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5939	Approved
0.7043	Intermediate Similarity	NPD5066	Phase 2
0.7043	Intermediate Similarity	NPD5936	Approved
0.7043	Intermediate Similarity	NPD5067	Phase 2
0.7042	Intermediate Similarity	NPD6641	Approved
0.7042	Intermediate Similarity	NPD6642	Approved
0.7037	Intermediate Similarity	NPD2091	Phase 2
0.7037	Intermediate Similarity	NPD2096	Phase 2
0.7028	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6790	Phase 1
0.7018	Intermediate Similarity	NPD4948	Discontinued
0.7017	Intermediate Similarity	NPD7426	Phase 1
0.7017	Intermediate Similarity	NPD3263	Phase 3
0.7009	Intermediate Similarity	NPD6874	Approved
0.7	Intermediate Similarity	NPD5913	Phase 3
0.7	Intermediate Similarity	NPD2844	Phase 3
0.7	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5479	Discontinued

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