NPASS Compound

Structure

NPC471304 OpenBabel07101719252D 27 31 0 0 1 0 0 0 0 0999 V2000 -1.6582 0.2085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9874 2.6752 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 -0.6942 0.4746 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 1.1942 0.9555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7718 -0.0192 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 3.8832 -0.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5943 1.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0181 -0.2272 0.0000 C 0 0 1 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 3.0172 -1.1921 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 3.0172 -2.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8011 0.0360 0.0000 C 0 0 2 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 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 -0.3985 1.6362 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 1 4 1 0 0 0 0 2 13 1 0 0 0 0 3 27 1 0 0 0 0 5 6 2 0 0 0 0 5 16 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 25 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 26 2 0 0 0 0 14 4 1 1 0 0 0 14 23 1 0 0 0 0 15 10 1 1 0 0 0 15 21 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 20 2 0 0 0 0 19 11 1 6 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 6 0 0 0 22 24 1 0 0 0 0 23 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.23
Volume:	389.974
LogP:	3.922
LogD:	4.202
LogS:	-4.219
# Rotatable Bonds:	4
TPSA:	45.33
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.878
Synthetic Accessibility Score:	5.31
Fsp3:	0.609
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:	-5.28
MDCK Permeability:	1.2610168596438598e-05
Pgp-inhibitor:	0.383
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.878
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	82.11884307861328%
Volume Distribution (VD):	2.298
Pgp-substrate:	9.804393768310547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.778
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.743
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.838
CYP2D6-inhibitor:	0.884
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	7.108
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.723
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.404
Carcinogencity:	0.543
Eye Corrosion:	0.009
Eye Irritation:	0.044
Respiratory Toxicity:	0.931

Download Data

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

Natural Product: NPC471304

Natural Product ID:	NPC471304
*Common Name:**	RJITZLAAWJSIDF-LGXLHQAVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RJITZLAAWJSIDF-LGXLHQAVSA-N
Standard InCHI:	InChI=1S/C23H30N2O2/c1-4-14-10-15-11-19-22-17(18-12-16(27-3)5-6-20(18)24-22)7-8-25(23(14)19)21(15)9-13(2)26/h5-6,12,14-15,19,21,23-24H,4,7-11H2,1-3H3/t14-,15-,19-,21+,23-/m0/s1
SMILES:	CCC1CC2CC3C1N(C2CC(=O)C)CCC4=C3NC5=C4C=C(C=C5)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409163
PubChem CID:	72191029
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
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944995]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26231157]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30169038]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	13010.0	nM	PMID[509979]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	13230.0	nM	PMID[509979]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	28530.0	nM	PMID[509979]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3880.0	nM	PMID[509979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14750.0	nM	PMID[509979]

☑ 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 NPC471304 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	446
0.1-0.2	2150
0.2-0.3	11542
0.3-0.4	7258
0.4-0.5	15329
0.5-0.6	3194
0.6-0.7	2135
0.7-0.8	569
0.8-0.85	43
0.85-0.9	23
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9536	High Similarity	NPC96321
0.9309	High Similarity	NPC329793
0.9158	High Similarity	NPC478078
0.9045	High Similarity	NPC473041
0.902	High Similarity	NPC311906
0.8981	High Similarity	NPC474192
0.8981	High Similarity	NPC475720
0.8945	High Similarity	NPC469928
0.8906	High Similarity	NPC329747
0.8844	High Similarity	NPC478074
0.8726	High Similarity	NPC475816
0.8685	High Similarity	NPC477066
0.8645	High Similarity	NPC478081
0.8645	High Similarity	NPC477067
0.8645	High Similarity	NPC473540
0.8645	High Similarity	NPC478082
0.8593	High Similarity	NPC475910
0.8511	High Similarity	NPC176127
0.8486	Intermediate Similarity	NPC17437
0.848	Intermediate Similarity	NPC330009
0.8429	Intermediate Similarity	NPC157931
0.8406	Intermediate Similarity	NPC472099
0.8404	Intermediate Similarity	NPC473105
0.84	Intermediate Similarity	NPC45190
0.84	Intermediate Similarity	NPC300156
0.839	Intermediate Similarity	NPC148183
0.839	Intermediate Similarity	NPC152768
0.8333	Intermediate Similarity	NPC472098
0.8299	Intermediate Similarity	NPC92111
0.8284	Intermediate Similarity	NPC208284
0.8261	Intermediate Similarity	NPC305984
0.8259	Intermediate Similarity	NPC478080
0.8247	Intermediate Similarity	NPC76748
0.8247	Intermediate Similarity	NPC329858
0.8227	Intermediate Similarity	NPC81939
0.8214	Intermediate Similarity	NPC307963
0.8209	Intermediate Similarity	NPC223427
0.8196	Intermediate Similarity	NPC296527
0.819	Intermediate Similarity	NPC475666
0.8173	Intermediate Similarity	NPC131017
0.815	Intermediate Similarity	NPC176538
0.8119	Intermediate Similarity	NPC162484
0.8104	Intermediate Similarity	NPC280799
0.8088	Intermediate Similarity	NPC53344
0.8075	Intermediate Similarity	NPC21638
0.8068	Intermediate Similarity	NPC94157
0.8066	Intermediate Similarity	NPC280272
0.8062	Intermediate Similarity	NPC478083
0.8061	Intermediate Similarity	NPC314333
0.806	Intermediate Similarity	NPC249040
0.8053	Intermediate Similarity	NPC329982
0.804	Intermediate Similarity	NPC251090
0.803	Intermediate Similarity	NPC476098
0.799	Intermediate Similarity	NPC276517
0.799	Intermediate Similarity	NPC84478
0.7963	Intermediate Similarity	NPC471762
0.7962	Intermediate Similarity	NPC46561
0.7962	Intermediate Similarity	NPC303658
0.7951	Intermediate Similarity	NPC472111
0.7945	Intermediate Similarity	NPC39370
0.7936	Intermediate Similarity	NPC473186
0.7923	Intermediate Similarity	NPC476116
0.7919	Intermediate Similarity	NPC242928
0.7917	Intermediate Similarity	NPC257851
0.7913	Intermediate Similarity	NPC249583
0.7913	Intermediate Similarity	NPC4687
0.7913	Intermediate Similarity	NPC193777
0.7902	Intermediate Similarity	NPC285558
0.7895	Intermediate Similarity	NPC264176
0.7892	Intermediate Similarity	NPC162730
0.7871	Intermediate Similarity	NPC72211
0.7857	Intermediate Similarity	NPC469592
0.7857	Intermediate Similarity	NPC39500
0.7857	Intermediate Similarity	NPC471080
0.7847	Intermediate Similarity	NPC187501
0.7837	Intermediate Similarity	NPC201697
0.7828	Intermediate Similarity	NPC63199
0.7828	Intermediate Similarity	NPC196251
0.7828	Intermediate Similarity	NPC111602
0.7828	Intermediate Similarity	NPC102338
0.7826	Intermediate Similarity	NPC321428
0.7822	Intermediate Similarity	NPC243834
0.7822	Intermediate Similarity	NPC70956
0.7816	Intermediate Similarity	NPC475070
0.7805	Intermediate Similarity	NPC474116
0.7804	Intermediate Similarity	NPC323969
0.7804	Intermediate Similarity	NPC132642
0.78	Intermediate Similarity	NPC55493
0.7798	Intermediate Similarity	NPC66777
0.7789	Intermediate Similarity	NPC472112
0.7784	Intermediate Similarity	NPC88363
0.7778	Intermediate Similarity	NPC475841
0.7778	Intermediate Similarity	NPC474145
0.7778	Intermediate Similarity	NPC122436
0.7773	Intermediate Similarity	NPC266931
0.7772	Intermediate Similarity	NPC70259
0.7767	Intermediate Similarity	NPC60621
0.7762	Intermediate Similarity	NPC87413
0.7756	Intermediate Similarity	NPC267423
0.7745	Intermediate Similarity	NPC128823
0.774	Intermediate Similarity	NPC270918
0.7731	Intermediate Similarity	NPC144452
0.7725	Intermediate Similarity	NPC48353
0.7725	Intermediate Similarity	NPC310211
0.7725	Intermediate Similarity	NPC308137
0.7723	Intermediate Similarity	NPC43787
0.7723	Intermediate Similarity	NPC205934
0.7721	Intermediate Similarity	NPC225279
0.772	Intermediate Similarity	NPC329688
0.772	Intermediate Similarity	NPC189812
0.7718	Intermediate Similarity	NPC199277
0.7718	Intermediate Similarity	NPC135887
0.7717	Intermediate Similarity	NPC194740
0.7713	Intermediate Similarity	NPC184680
0.771	Intermediate Similarity	NPC184408
0.771	Intermediate Similarity	NPC469594
0.7707	Intermediate Similarity	NPC315491
0.7707	Intermediate Similarity	NPC45459
0.7704	Intermediate Similarity	NPC474798
0.7703	Intermediate Similarity	NPC476465
0.7703	Intermediate Similarity	NPC82548
0.7685	Intermediate Similarity	NPC198503
0.7679	Intermediate Similarity	NPC470784
0.7679	Intermediate Similarity	NPC470785
0.7679	Intermediate Similarity	NPC101350
0.7678	Intermediate Similarity	NPC9894
0.7674	Intermediate Similarity	NPC208084
0.767	Intermediate Similarity	NPC476044
0.767	Intermediate Similarity	NPC232727
0.7668	Intermediate Similarity	NPC295228
0.7664	Intermediate Similarity	NPC169402
0.7653	Intermediate Similarity	NPC116238
0.765	Intermediate Similarity	NPC246700
0.7647	Intermediate Similarity	NPC474688
0.7639	Intermediate Similarity	NPC150239
0.7638	Intermediate Similarity	NPC171171
0.7634	Intermediate Similarity	NPC235685
0.7633	Intermediate Similarity	NPC475085
0.7633	Intermediate Similarity	NPC475112
0.7633	Intermediate Similarity	NPC291535
0.763	Intermediate Similarity	NPC199667
0.763	Intermediate Similarity	NPC123976
0.763	Intermediate Similarity	NPC470020
0.763	Intermediate Similarity	NPC167860
0.7629	Intermediate Similarity	NPC303374
0.7624	Intermediate Similarity	NPC472113
0.7624	Intermediate Similarity	NPC99666
0.7621	Intermediate Similarity	NPC315957
0.7621	Intermediate Similarity	NPC213308
0.7617	Intermediate Similarity	NPC170114
0.7613	Intermediate Similarity	NPC49547
0.76	Intermediate Similarity	NPC41679
0.7598	Intermediate Similarity	NPC13880
0.7596	Intermediate Similarity	NPC245816
0.7596	Intermediate Similarity	NPC476138
0.7591	Intermediate Similarity	NPC473185
0.7591	Intermediate Similarity	NPC74575
0.7588	Intermediate Similarity	NPC314002
0.7586	Intermediate Similarity	NPC475190
0.7583	Intermediate Similarity	NPC473181
0.7573	Intermediate Similarity	NPC241024
0.757	Intermediate Similarity	NPC470549
0.7562	Intermediate Similarity	NPC128751
0.7561	Intermediate Similarity	NPC156704
0.7559	Intermediate Similarity	NPC475778
0.7559	Intermediate Similarity	NPC473180
0.7559	Intermediate Similarity	NPC316981
0.7557	Intermediate Similarity	NPC274640
0.7556	Intermediate Similarity	NPC6786
0.755	Intermediate Similarity	NPC160381
0.7548	Intermediate Similarity	NPC295898
0.7546	Intermediate Similarity	NPC247803
0.7545	Intermediate Similarity	NPC470018
0.7538	Intermediate Similarity	NPC312872
0.7538	Intermediate Similarity	NPC204717
0.7536	Intermediate Similarity	NPC39679
0.7536	Intermediate Similarity	NPC254240
0.7536	Intermediate Similarity	NPC312870
0.7536	Intermediate Similarity	NPC294909
0.7536	Intermediate Similarity	NPC128265
0.7536	Intermediate Similarity	NPC199851
0.7535	Intermediate Similarity	NPC74969
0.7532	Intermediate Similarity	NPC284685
0.7525	Intermediate Similarity	NPC106833
0.7525	Intermediate Similarity	NPC469497
0.7524	Intermediate Similarity	NPC476106
0.7524	Intermediate Similarity	NPC306376
0.7513	Intermediate Similarity	NPC26850
0.7512	Intermediate Similarity	NPC213530
0.7512	Intermediate Similarity	NPC193267
0.7512	Intermediate Similarity	NPC74360
0.7511	Intermediate Similarity	NPC473187
0.75	Intermediate Similarity	NPC329631
0.75	Intermediate Similarity	NPC179287
0.75	Intermediate Similarity	NPC191489
0.7489	Intermediate Similarity	NPC260434
0.7489	Intermediate Similarity	NPC475253
0.7488	Intermediate Similarity	NPC118228
0.7488	Intermediate Similarity	NPC88008
0.7488	Intermediate Similarity	NPC477065

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 NPC471304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	607
0.2-0.3	785
0.3-0.4	1239
0.4-0.5	2573
0.5-0.6	2491
0.6-0.7	1022
0.7-0.8	176
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9462	High Similarity	NPD4118	Clinical (unspecified phase)
0.8486	Intermediate Similarity	NPD8358	Approved
0.8408	Intermediate Similarity	NPD5658	Approved
0.8406	Intermediate Similarity	NPD6242	Discontinued
0.8214	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1038	Approved
0.8173	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD4885	Approved
0.8061	Intermediate Similarity	NPD4499	Approved
0.799	Intermediate Similarity	NPD4418	Discontinued
0.7981	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD7452	Approved
0.7913	Intermediate Similarity	NPD7453	Approved
0.7826	Intermediate Similarity	NPD7222	Phase 2
0.7814	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8016	Phase 3
0.7798	Intermediate Similarity	NPD5559	Phase 2
0.7778	Intermediate Similarity	NPD3003	Approved
0.7743	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5293	Phase 2
0.7729	Intermediate Similarity	NPD4795	Phase 2
0.771	Intermediate Similarity	NPD5632	Approved
0.771	Intermediate Similarity	NPD4429	Discontinued
0.7707	Intermediate Similarity	NPD484	Approved
0.7703	Intermediate Similarity	NPD2187	Approved
0.7703	Intermediate Similarity	NPD2189	Approved
0.77	Intermediate Similarity	NPD5612	Discontinued
0.7696	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD3825	Phase 3
0.7647	Intermediate Similarity	NPD5003	Discontinued
0.7621	Intermediate Similarity	NPD1739	Approved
0.7621	Intermediate Similarity	NPD1740	Approved
0.7619	Intermediate Similarity	NPD2916	Discontinued
0.7617	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5913	Phase 3
0.7573	Intermediate Similarity	NPD1768	Approved
0.7546	Intermediate Similarity	NPD3354	Phase 2
0.7536	Intermediate Similarity	NPD4501	Approved
0.7536	Intermediate Similarity	NPD4500	Approved
0.7532	Intermediate Similarity	NPD7955	Approved
0.7532	Intermediate Similarity	NPD7956	Approved
0.7525	Intermediate Similarity	NPD4203	Approved
0.7525	Intermediate Similarity	NPD4204	Approved
0.7524	Intermediate Similarity	NPD5530	Phase 1
0.7523	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD3920	Phase 2
0.7512	Intermediate Similarity	NPD7194	Discontinued
0.7512	Intermediate Similarity	NPD5512	Phase 3
0.75	Intermediate Similarity	NPD8363	Approved
0.75	Intermediate Similarity	NPD8364	Approved
0.75	Intermediate Similarity	NPD7708	Approved
0.75	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD4558	Phase 2
0.7488	Intermediate Similarity	NPD3257	Approved
0.7488	Intermediate Similarity	NPD5902	Approved
0.7488	Intermediate Similarity	NPD5903	Approved
0.7477	Intermediate Similarity	NPD5930	Phase 3
0.7476	Intermediate Similarity	NPD32	Approved
0.7476	Intermediate Similarity	NPD4122	Approved
0.7476	Intermediate Similarity	NPD4034	Approved
0.7476	Intermediate Similarity	NPD4039	Approved
0.7476	Intermediate Similarity	NPD4035	Approved
0.7476	Intermediate Similarity	NPD4038	Approved
0.7476	Intermediate Similarity	NPD4036	Approved
0.7476	Intermediate Similarity	NPD4037	Approved
0.7476	Intermediate Similarity	NPD4033	Approved
0.7476	Intermediate Similarity	NPD31	Approved
0.7463	Intermediate Similarity	NPD5256	Discontinued
0.7452	Intermediate Similarity	NPD4601	Approved
0.7452	Intermediate Similarity	NPD4600	Approved
0.7444	Intermediate Similarity	NPD5479	Discontinued
0.7441	Intermediate Similarity	NPD8403	Phase 1
0.7438	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3006	Discontinued
0.7431	Intermediate Similarity	NPD3258	Approved
0.743	Intermediate Similarity	NPD5416	Discontinued
0.743	Intermediate Similarity	NPD4502	Phase 2
0.7419	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD5429	Discontinued
0.7399	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1326	Approved
0.7385	Intermediate Similarity	NPD6985	Discontinued
0.7385	Intermediate Similarity	NPD1325	Approved
0.7385	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6790	Phase 1
0.7375	Intermediate Similarity	NPD7803	Approved
0.7373	Intermediate Similarity	NPD3393	Approved
0.7373	Intermediate Similarity	NPD3389	Approved
0.7373	Intermediate Similarity	NPD3394	Approved
0.7371	Intermediate Similarity	NPD2509	Approved
0.7371	Intermediate Similarity	NPD6376	Discontinued
0.7371	Intermediate Similarity	NPD2510	Approved
0.7366	Intermediate Similarity	NPD4952	Phase 3
0.7366	Intermediate Similarity	NPD3924	Approved
0.7366	Intermediate Similarity	NPD5022	Discontinued
0.7366	Intermediate Similarity	NPD3921	Approved
0.7366	Intermediate Similarity	NPD3923	Approved
0.7366	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3922	Approved
0.7358	Intermediate Similarity	NPD5601	Phase 2
0.7358	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7994	Phase 2
0.7353	Intermediate Similarity	NPD2564	Approved
0.7353	Intermediate Similarity	NPD2565	Phase 2
0.7347	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4511	Phase 1
0.7327	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1392	Approved
0.7318	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8466	Approved
0.7317	Intermediate Similarity	NPD8465	Approved
0.7317	Intermediate Similarity	NPD8467	Approved
0.7313	Intermediate Similarity	NPD6964	Approved
0.7313	Intermediate Similarity	NPD6963	Approved
0.7308	Intermediate Similarity	NPD5482	Discontinued
0.7295	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5670	Approved
0.728	Intermediate Similarity	NPD6531	Approved
0.728	Intermediate Similarity	NPD6530	Approved
0.7277	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3402	Phase 1
0.7269	Intermediate Similarity	NPD4373	Phase 2
0.7269	Intermediate Similarity	NPD8091	Phase 3
0.7269	Intermediate Similarity	NPD7470	Discontinued
0.7269	Intermediate Similarity	NPD6220	Phase 3
0.7264	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8100	Phase 3
0.7248	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4897	Phase 2
0.7235	Intermediate Similarity	NPD7069	Discontinued
0.7232	Intermediate Similarity	NPD7603	Discontinued
0.7228	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7797	Approved
0.7225	Intermediate Similarity	NPD7948	Phase 1
0.7225	Intermediate Similarity	NPD7796	Approved
0.7215	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5473	Discontinued
0.7212	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4154	Approved
0.7209	Intermediate Similarity	NPD3853	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8460	Approved
0.72	Intermediate Similarity	NPD8425	Approved
0.72	Intermediate Similarity	NPD8459	Approved
0.72	Intermediate Similarity	NPD4328	Approved
0.72	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3259	Approved
0.72	Intermediate Similarity	NPD8426	Approved
0.7191	Intermediate Similarity	NPD8102	Discontinued
0.7189	Intermediate Similarity	NPD5067	Phase 2
0.7189	Intermediate Similarity	NPD5066	Phase 2
0.7188	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5065	Approved
0.7184	Intermediate Similarity	NPD2410	Phase 2
0.7183	Intermediate Similarity	NPD6991	Approved
0.7179	Intermediate Similarity	NPD5488	Discontinued
0.7177	Intermediate Similarity	NPD8427	Approved
0.7177	Intermediate Similarity	NPD6550	Discontinued
0.7177	Intermediate Similarity	NPD8429	Approved
0.7177	Intermediate Similarity	NPD8428	Approved
0.7175	Intermediate Similarity	NPD7221	Approved
0.7175	Intermediate Similarity	NPD7219	Approved
0.7168	Intermediate Similarity	NPD5014	Discontinued
0.7163	Intermediate Similarity	NPD802	Phase 2
0.7161	Intermediate Similarity	NPD8101	Phase 3
0.7157	Intermediate Similarity	NPD4889	Approved
0.7156	Intermediate Similarity	NPD3816	Phase 1
0.7156	Intermediate Similarity	NPD3815	Phase 1
0.715	Intermediate Similarity	NPD5901	Discontinued
0.715	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6276	Discontinued
0.7149	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7395	Discontinued
0.7143	Intermediate Similarity	NPD8463	Approved
0.7136	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7671	Approved
0.713	Intermediate Similarity	NPD7672	Approved
0.7129	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6590	Discontinued
0.7124	Intermediate Similarity	NPD6517	Phase 3
0.7123	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3945	Discontinued
0.7118	Intermediate Similarity	NPD7558	Phase 2
0.7117	Intermediate Similarity	NPD6770	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