NPASS Compound

Structure

NPC160570 OpenBabel07101718222D 29 33 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 19 5 1 6 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 23 25 1 6 0 0 0 24 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	395.17
Volume:	400.075
LogP:	2.684
LogD:	2.126
LogS:	-2.11
# Rotatable Bonds:	3
TPSA:	70.98
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	3.989
Fsp3:	0.391
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:	-5.766
MDCK Permeability:	1.6236310329986736e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.714
20% Bioavailability (F20%):	0.713
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	77.09040069580078%
Volume Distribution (VD):	1.926
Pgp-substrate:	15.143312454223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.867

ADMET: Excretion

Clearance (CL):	8.861
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.641
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.801
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC160570

Natural Product ID:	NPC160570
*Common Name:**	(-)-10Beta,13Aalpha-14Beta-Hydroxyantofine N-Oxide
IUPAC Name:	(13aR,14R)-2,3,6-trimethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium-14-ol
Synonyms:
Standard InCHIKey:	LDYKNAJDTNPEPC-DHFLCVKNSA-N
Standard InCHI:	InChI=1S/C23H25NO5/c1-27-13-6-7-14-15(9-13)16-10-20(28-2)21(29-3)11-17(16)22-18(14)12-24(26)8-4-5-19(24)23(22)25/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23+,24?/m1/s1
SMILES:	COc1ccc2c(c1)c1cc(c(cc1c1c2CN2(=O)CCC[C@@H]2[C@@H]1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479473
PubChem CID:	11741391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087617]
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]

☑ 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
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	100.0	nM	PMID[567378]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	160.0	nM	PMID[567378]

☑ 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 NPC160570 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	312
0.1-0.2	1369
0.2-0.3	4957
0.3-0.4	12575
0.4-0.5	5880
0.5-0.6	12793
0.6-0.7	3915
0.7-0.8	672
0.8-0.85	196
0.85-0.9	16
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC329911
0.9806	High Similarity	NPC76116
0.962	High Similarity	NPC164429
0.9172	High Similarity	NPC477133
0.9172	High Similarity	NPC477132
0.9032	High Similarity	NPC44869
0.8957	High Similarity	NPC150879
0.8773	High Similarity	NPC233650
0.8765	High Similarity	NPC233718
0.872	High Similarity	NPC134858
0.8614	High Similarity	NPC210140
0.8494	Intermediate Similarity	NPC169743
0.8364	Intermediate Similarity	NPC59028
0.8364	Intermediate Similarity	NPC92191
0.8313	Intermediate Similarity	NPC205167
0.8313	Intermediate Similarity	NPC249274
0.8303	Intermediate Similarity	NPC475326
0.8282	Intermediate Similarity	NPC37272
0.8282	Intermediate Similarity	NPC470924
0.8246	Intermediate Similarity	NPC470739
0.8246	Intermediate Similarity	NPC477640
0.8246	Intermediate Similarity	NPC225597
0.8235	Intermediate Similarity	NPC58766
0.8235	Intermediate Similarity	NPC290759
0.8235	Intermediate Similarity	NPC266176
0.8235	Intermediate Similarity	NPC82533
0.8235	Intermediate Similarity	NPC475686
0.8235	Intermediate Similarity	NPC158148
0.8229	Intermediate Similarity	NPC248642
0.8218	Intermediate Similarity	NPC126284
0.8194	Intermediate Similarity	NPC475828
0.8187	Intermediate Similarity	NPC474475
0.8182	Intermediate Similarity	NPC244112
0.8182	Intermediate Similarity	NPC156576
0.8171	Intermediate Similarity	NPC26601
0.8153	Intermediate Similarity	NPC210086
0.8133	Intermediate Similarity	NPC186063
0.8133	Intermediate Similarity	NPC147091
0.8098	Intermediate Similarity	NPC219162
0.8092	Intermediate Similarity	NPC2314
0.807	Intermediate Similarity	NPC181653
0.807	Intermediate Similarity	NPC100566
0.807	Intermediate Similarity	NPC190332
0.8049	Intermediate Similarity	NPC274026
0.8047	Intermediate Similarity	NPC60186
0.8037	Intermediate Similarity	NPC130941
0.8	Intermediate Similarity	NPC320104
0.8	Intermediate Similarity	NPC474470
0.7989	Intermediate Similarity	NPC214116
0.7988	Intermediate Similarity	NPC4304
0.7976	Intermediate Similarity	NPC148014
0.7976	Intermediate Similarity	NPC78359
0.7976	Intermediate Similarity	NPC40389
0.7976	Intermediate Similarity	NPC65490
0.7976	Intermediate Similarity	NPC315707
0.7975	Intermediate Similarity	NPC253883
0.7975	Intermediate Similarity	NPC95075
0.7975	Intermediate Similarity	NPC90844
0.7965	Intermediate Similarity	NPC158376
0.7965	Intermediate Similarity	NPC474931
0.7965	Intermediate Similarity	NPC306555
0.7965	Intermediate Similarity	NPC81218
0.7965	Intermediate Similarity	NPC12053
0.7965	Intermediate Similarity	NPC117188
0.7965	Intermediate Similarity	NPC205421
0.7965	Intermediate Similarity	NPC145832
0.7953	Intermediate Similarity	NPC212794
0.7953	Intermediate Similarity	NPC96603
0.7953	Intermediate Similarity	NPC13504
0.7953	Intermediate Similarity	NPC253043
0.7953	Intermediate Similarity	NPC306843
0.7953	Intermediate Similarity	NPC196447
0.7953	Intermediate Similarity	NPC78222
0.7953	Intermediate Similarity	NPC136508
0.7953	Intermediate Similarity	NPC477563
0.7931	Intermediate Similarity	NPC57272
0.791	Intermediate Similarity	NPC244554
0.7907	Intermediate Similarity	NPC476002
0.7898	Intermediate Similarity	NPC237044
0.7895	Intermediate Similarity	NPC324144
0.7882	Intermediate Similarity	NPC97072
0.7882	Intermediate Similarity	NPC215829
0.787	Intermediate Similarity	NPC476572
0.7861	Intermediate Similarity	NPC301189
0.7861	Intermediate Similarity	NPC298186
0.7861	Intermediate Similarity	NPC252960
0.7857	Intermediate Similarity	NPC99659
0.7857	Intermediate Similarity	NPC325871
0.7853	Intermediate Similarity	NPC320223
0.7853	Intermediate Similarity	NPC114364
0.7853	Intermediate Similarity	NPC474325
0.7853	Intermediate Similarity	NPC118633
0.7853	Intermediate Similarity	NPC148693
0.7853	Intermediate Similarity	NPC294790
0.7853	Intermediate Similarity	NPC477560
0.7853	Intermediate Similarity	NPC185838
0.7849	Intermediate Similarity	NPC247972
0.7844	Intermediate Similarity	NPC133011
0.7844	Intermediate Similarity	NPC82285
0.7841	Intermediate Similarity	NPC199465
0.7841	Intermediate Similarity	NPC304675
0.7841	Intermediate Similarity	NPC128560
0.7841	Intermediate Similarity	NPC229166
0.7821	Intermediate Similarity	NPC476575
0.7818	Intermediate Similarity	NPC428
0.7818	Intermediate Similarity	NPC246587
0.7818	Intermediate Similarity	NPC476571
0.7818	Intermediate Similarity	NPC135538
0.7818	Intermediate Similarity	NPC24233
0.7818	Intermediate Similarity	NPC147390
0.7811	Intermediate Similarity	NPC160931
0.7811	Intermediate Similarity	NPC37205
0.7809	Intermediate Similarity	NPC474745
0.7803	Intermediate Similarity	NPC124657
0.7803	Intermediate Similarity	NPC476432
0.7803	Intermediate Similarity	NPC24264
0.7797	Intermediate Similarity	NPC241704
0.7791	Intermediate Similarity	NPC218614
0.7791	Intermediate Similarity	NPC1229
0.7778	Intermediate Similarity	NPC18402
0.7778	Intermediate Similarity	NPC27410
0.7778	Intermediate Similarity	NPC166014
0.7771	Intermediate Similarity	NPC92541
0.7765	Intermediate Similarity	NPC129603
0.7759	Intermediate Similarity	NPC247389
0.7759	Intermediate Similarity	NPC298979
0.7758	Intermediate Similarity	NPC321505
0.7758	Intermediate Similarity	NPC191376
0.7758	Intermediate Similarity	NPC476151
0.7758	Intermediate Similarity	NPC179825
0.775	Intermediate Similarity	NPC193528
0.7746	Intermediate Similarity	NPC302527
0.7746	Intermediate Similarity	NPC225774
0.7746	Intermediate Similarity	NPC16805
0.7746	Intermediate Similarity	NPC167546
0.7744	Intermediate Similarity	NPC130926
0.7736	Intermediate Similarity	NPC11147
0.7727	Intermediate Similarity	NPC239775
0.7727	Intermediate Similarity	NPC10871
0.7725	Intermediate Similarity	NPC88249
0.7725	Intermediate Similarity	NPC151895
0.7725	Intermediate Similarity	NPC192768
0.7725	Intermediate Similarity	NPC220858
0.7725	Intermediate Similarity	NPC97221
0.7717	Intermediate Similarity	NPC117717
0.7716	Intermediate Similarity	NPC474915
0.7716	Intermediate Similarity	NPC328750
0.7716	Intermediate Similarity	NPC188163
0.7716	Intermediate Similarity	NPC213206
0.7709	Intermediate Similarity	NPC32154
0.7706	Intermediate Similarity	NPC323443
0.7706	Intermediate Similarity	NPC180756
0.7701	Intermediate Similarity	NPC219341
0.7688	Intermediate Similarity	NPC124433
0.7688	Intermediate Similarity	NPC293871
0.7684	Intermediate Similarity	NPC477020
0.7684	Intermediate Similarity	NPC192135
0.7684	Intermediate Similarity	NPC66341
0.768	Intermediate Similarity	NPC474746
0.768	Intermediate Similarity	NPC475981
0.7679	Intermediate Similarity	NPC81733
0.7679	Intermediate Similarity	NPC326316
0.767	Intermediate Similarity	NPC26240
0.767	Intermediate Similarity	NPC311991
0.767	Intermediate Similarity	NPC168753
0.767	Intermediate Similarity	NPC477562
0.767	Intermediate Similarity	NPC69712
0.767	Intermediate Similarity	NPC118274
0.7665	Intermediate Similarity	NPC103379
0.7665	Intermediate Similarity	NPC477565
0.7657	Intermediate Similarity	NPC474324
0.7657	Intermediate Similarity	NPC57812
0.7657	Intermediate Similarity	NPC210918
0.7654	Intermediate Similarity	NPC314682
0.7651	Intermediate Similarity	NPC144863
0.7647	Intermediate Similarity	NPC189266
0.7647	Intermediate Similarity	NPC76079
0.7647	Intermediate Similarity	NPC127674
0.7647	Intermediate Similarity	NPC295691
0.7647	Intermediate Similarity	NPC193949
0.7647	Intermediate Similarity	NPC5238
0.7647	Intermediate Similarity	NPC204828
0.7647	Intermediate Similarity	NPC469817
0.7647	Intermediate Similarity	NPC249797
0.7647	Intermediate Similarity	NPC78733
0.7647	Intermediate Similarity	NPC278799
0.7647	Intermediate Similarity	NPC207757
0.7647	Intermediate Similarity	NPC276588
0.7647	Intermediate Similarity	NPC54379
0.7647	Intermediate Similarity	NPC172765
0.7647	Intermediate Similarity	NPC184026
0.7647	Intermediate Similarity	NPC2413
0.7647	Intermediate Similarity	NPC110416
0.7647	Intermediate Similarity	NPC39701
0.764	Intermediate Similarity	NPC187678
0.764	Intermediate Similarity	NPC49353
0.7624	Intermediate Similarity	NPC116284
0.7622	Intermediate Similarity	NPC128019
0.7622	Intermediate Similarity	NPC476567
0.7622	Intermediate Similarity	NPC136860

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 NPC160570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	668
0.2-0.3	911
0.3-0.4	2061
0.4-0.5	2653
0.5-0.6	1806
0.6-0.7	716
0.7-0.8	143
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7976	Intermediate Similarity	NPD2560	Approved
0.7976	Intermediate Similarity	NPD2563	Approved
0.7917	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD2970	Approved
0.7861	Intermediate Similarity	NPD2969	Approved
0.7803	Intermediate Similarity	NPD6071	Discontinued
0.7791	Intermediate Similarity	NPD5241	Discontinued
0.7778	Intermediate Similarity	NPD4237	Approved
0.7778	Intermediate Similarity	NPD4236	Phase 3
0.7716	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2489	Approved
0.7714	Intermediate Similarity	NPD27	Approved
0.7701	Intermediate Similarity	NPD3051	Approved
0.7588	Intermediate Similarity	NPD4772	Phase 2
0.7588	Intermediate Similarity	NPD4773	Phase 2
0.7586	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7831	Phase 2
0.7572	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7833	Phase 2
0.7569	Intermediate Similarity	NPD7311	Approved
0.7569	Intermediate Similarity	NPD7310	Approved
0.7569	Intermediate Similarity	NPD7312	Approved
0.7569	Intermediate Similarity	NPD7313	Approved
0.7545	Intermediate Similarity	NPD4584	Approved
0.7527	Intermediate Similarity	NPD7309	Approved
0.75	Intermediate Similarity	NPD7906	Approved
0.7455	Intermediate Similarity	NPD3060	Approved
0.7446	Intermediate Similarity	NPD4663	Approved
0.7416	Intermediate Similarity	NPD4481	Phase 3
0.7416	Intermediate Similarity	NPD2898	Approved
0.7414	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD5773	Approved
0.7399	Intermediate Similarity	NPD5772	Approved
0.7377	Intermediate Similarity	NPD4577	Approved
0.7377	Intermediate Similarity	NPD4578	Approved
0.7299	Intermediate Similarity	NPD2977	Approved
0.7299	Intermediate Similarity	NPD2978	Approved
0.7267	Intermediate Similarity	NPD4005	Discontinued
0.7262	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4210	Discontinued
0.7205	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4017	Approved
0.7151	Intermediate Similarity	NPD3640	Phase 3
0.7151	Intermediate Similarity	NPD6030	Approved
0.7151	Intermediate Similarity	NPD6031	Approved
0.7151	Intermediate Similarity	NPD3641	Approved
0.7151	Intermediate Similarity	NPD3639	Approved
0.7151	Intermediate Similarity	NPD8054	Approved
0.7151	Intermediate Similarity	NPD8053	Approved
0.7143	Intermediate Similarity	NPD7298	Approved
0.7135	Intermediate Similarity	NPD5709	Phase 3
0.7135	Intermediate Similarity	NPD7400	Phase 3
0.7135	Intermediate Similarity	NPD4123	Phase 3
0.7135	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3533	Approved
0.7128	Intermediate Similarity	NPD2972	Approved
0.7118	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4010	Discontinued
0.7104	Intermediate Similarity	NPD8156	Discontinued
0.7101	Intermediate Similarity	NPD6331	Phase 2
0.71	Intermediate Similarity	NPD5676	Approved
0.7095	Intermediate Similarity	NPD4666	Phase 3
0.7093	Intermediate Similarity	NPD6090	Discontinued
0.7083	Intermediate Similarity	NPD7037	Approved
0.7076	Intermediate Similarity	NPD2421	Approved
0.7076	Intermediate Similarity	NPD2420	Approved
0.7059	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6107	Approved
0.7052	Intermediate Similarity	NPD5976	Discontinued
0.7049	Intermediate Similarity	NPD8252	Approved
0.7049	Intermediate Similarity	NPD8251	Approved
0.7049	Intermediate Similarity	NPD8099	Discontinued
0.7047	Intermediate Similarity	NPD2975	Approved
0.7047	Intermediate Similarity	NPD2973	Approved
0.7047	Intermediate Similarity	NPD2974	Approved
0.7041	Intermediate Similarity	NPD4162	Approved
0.7041	Intermediate Similarity	NPD2491	Approved
0.7041	Intermediate Similarity	NPD3448	Approved
0.7041	Intermediate Similarity	NPD3057	Approved
0.7022	Intermediate Similarity	NPD6788	Approved
0.7011	Intermediate Similarity	NPD3687	Approved
0.7011	Intermediate Similarity	NPD3686	Approved
0.6995	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3450	Approved
0.699	Remote Similarity	NPD2494	Approved
0.699	Remote Similarity	NPD2493	Approved
0.699	Remote Similarity	NPD3452	Approved
0.6971	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2238	Phase 2
0.6963	Remote Similarity	NPD2488	Approved
0.6963	Remote Similarity	NPD2490	Approved
0.6947	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5177	Phase 3
0.6939	Remote Similarity	NPD4580	Approved
0.6935	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6297	Approved
0.6933	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4675	Approved
0.6932	Remote Similarity	NPD4678	Approved
0.6923	Remote Similarity	NPD4166	Phase 2
0.6919	Remote Similarity	NPD3845	Phase 1
0.6915	Remote Similarity	NPD2971	Approved
0.6915	Remote Similarity	NPD2968	Approved
0.6909	Remote Similarity	NPD2674	Phase 3
0.6907	Remote Similarity	NPD5582	Discontinued
0.6905	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4055	Discovery
0.6885	Remote Similarity	NPD6688	Approved
0.6885	Remote Similarity	NPD6687	Approved
0.6884	Remote Similarity	NPD4583	Approved
0.6884	Remote Similarity	NPD4582	Approved
0.6878	Remote Similarity	NPD6851	Approved
0.6878	Remote Similarity	NPD6853	Approved
0.6862	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2677	Approved
0.6848	Remote Similarity	NPD5718	Phase 2
0.6845	Remote Similarity	NPD6895	Approved
0.6845	Remote Similarity	NPD6896	Approved
0.6837	Remote Similarity	NPD4420	Approved
0.6834	Remote Similarity	NPD4004	Approved
0.6834	Remote Similarity	NPD4002	Approved
0.6828	Remote Similarity	NPD42	Phase 2
0.6828	Remote Similarity	NPD6042	Phase 2
0.6824	Remote Similarity	NPD1375	Discontinued
0.6821	Remote Similarity	NPD6666	Approved
0.6821	Remote Similarity	NPD6667	Approved
0.6821	Remote Similarity	NPD7124	Phase 2
0.6818	Remote Similarity	NPD4482	Phase 3
0.6813	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7038	Approved
0.6809	Remote Similarity	NPD7039	Approved
0.6805	Remote Similarity	NPD1753	Discontinued
0.6798	Remote Similarity	NPD6072	Discontinued
0.6788	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1774	Approved
0.6782	Remote Similarity	NPD3124	Discontinued
0.6776	Remote Similarity	NPD7802	Discontinued
0.6772	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD3398	Discontinued
0.6771	Remote Similarity	NPD4157	Discontinued
0.6768	Remote Similarity	NPD4107	Approved
0.6766	Remote Similarity	NPD3109	Approved
0.6766	Remote Similarity	NPD3110	Approved
0.6765	Remote Similarity	NPD2161	Phase 2
0.6763	Remote Similarity	NPD3692	Discontinued
0.6761	Remote Similarity	NPD2122	Discontinued
0.6747	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD601	Approved
0.6747	Remote Similarity	NPD3144	Approved
0.6747	Remote Similarity	NPD3145	Approved
0.6747	Remote Similarity	NPD598	Approved
0.6747	Remote Similarity	NPD597	Approved
0.6743	Remote Similarity	NPD1424	Approved
0.6738	Remote Similarity	NPD5313	Approved
0.6738	Remote Similarity	NPD5312	Approved
0.6737	Remote Similarity	NPD7280	Phase 3
0.6737	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7281	Phase 3
0.6714	Remote Similarity	NPD7907	Approved
0.6707	Remote Similarity	NPD4474	Approved
0.6707	Remote Similarity	NPD1136	Approved
0.6707	Remote Similarity	NPD1130	Approved
0.6707	Remote Similarity	NPD4475	Approved
0.6707	Remote Similarity	NPD1132	Approved
0.6703	Remote Similarity	NPD2388	Discontinued
0.6703	Remote Similarity	NPD5604	Discontinued
0.6702	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5006	Approved
0.67	Remote Similarity	NPD4859	Phase 1
0.67	Remote Similarity	NPD5005	Approved
0.6699	Remote Similarity	NPD4665	Approved
0.6699	Remote Similarity	NPD4111	Phase 1
0.6686	Remote Similarity	NPD7153	Discontinued
0.6686	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3054	Approved
0.6686	Remote Similarity	NPD3052	Approved
0.6686	Remote Similarity	NPD823	Approved
0.6686	Remote Similarity	NPD817	Approved
0.6684	Remote Similarity	NPD7291	Discontinued
0.6682	Remote Similarity	NPD6997	Phase 2
0.6667	Remote Similarity	NPD3062	Approved
0.6667	Remote Similarity	NPD1914	Approved
0.6667	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD3061	Approved
0.6667	Remote Similarity	NPD5160	Discontinued
0.6649	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2874	Phase 2
0.6648	Remote Similarity	NPD3645	Discontinued
0.6647	Remote Similarity	NPD1039	Discontinued
0.6646	Remote Similarity	NPD4103	Phase 2
0.6646	Remote Similarity	NPD4104	Clinical (unspecified phase)

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