NPASS Compound

Structure

NPC475828 OpenBabel07101719252D 28 31 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -4.4152 3.3090 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 -2.5981 1.5000 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 -0.8660 3.5000 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 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -1.7321 3.0000 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 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 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 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 6 9 1 0 0 0 0 6 16 2 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 5 1 1 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 22 23 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	381.19
Volume:	399.841
LogP:	3.432
LogD:	2.903
LogS:	-1.803
# Rotatable Bonds:	5
TPSA:	50.75
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	3.573
Fsp3:	0.391
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:	-5.473
MDCK Permeability:	4.021342465421185e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.933
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	60.057518005371094%
Volume Distribution (VD):	2.566
Pgp-substrate:	21.30838966369629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.535
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.194
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	11.778
Half-life (T1/2):	0.951

ADMET: Toxicity

hERG Blockers:	0.578
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.409
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.716
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC475828

Natural Product ID:	NPC475828
*Common Name:**	(-)-10Beta,13Aalpha-Secoantofine N-Oxide
IUPAC Name:	(8aR)-7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-4-oxido-1,2,3,5,8,8a-hexahydroindolizin-4-ium
Synonyms:
Standard InCHIKey:	LKJDIDQKBASUHE-QFADGXAASA-N
Standard InCHI:	InChI=1S/C23H27NO4/c1-26-19-9-6-16(7-10-19)21-15-24(25)12-4-5-18(24)14-20(21)17-8-11-22(27-2)23(13-17)28-3/h6-11,13,18H,4-5,12,14-15H2,1-3H3/t18-,24?/m1/s1
SMILES:	COc1ccc(cc1)C1=C(C[C@@H]2N(=O)(C1)CCC2)c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516914
PubChem CID:	10643559
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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	=	2550.0	nM	PMID[481451]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3300.0	nM	PMID[481451]

☑ 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 NPC475828 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	274
0.1-0.2	1489
0.2-0.3	8359
0.3-0.4	9869
0.4-0.5	7313
0.5-0.6	11358
0.6-0.7	3193
0.7-0.8	783
0.8-0.85	53
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC118419
0.9098	High Similarity	NPC11147
0.9071	High Similarity	NPC44869
0.8824	High Similarity	NPC193528
0.8571	High Similarity	NPC477132
0.8571	High Similarity	NPC477133
0.8357	Intermediate Similarity	NPC210086
0.8355	Intermediate Similarity	NPC76116
0.8194	Intermediate Similarity	NPC160570
0.8194	Intermediate Similarity	NPC164429
0.8121	Intermediate Similarity	NPC470924
0.8121	Intermediate Similarity	NPC37272
0.8112	Intermediate Similarity	NPC474915
0.8112	Intermediate Similarity	NPC328750
0.8112	Intermediate Similarity	NPC213206
0.8112	Intermediate Similarity	NPC188163
0.8042	Intermediate Similarity	NPC314682
0.8029	Intermediate Similarity	NPC172403
0.8027	Intermediate Similarity	NPC253883
0.8027	Intermediate Similarity	NPC95075
0.8027	Intermediate Similarity	NPC90844
0.8026	Intermediate Similarity	NPC475326
0.8025	Intermediate Similarity	NPC329911
0.7973	Intermediate Similarity	NPC475959
0.7919	Intermediate Similarity	NPC219162
0.7891	Intermediate Similarity	NPC130926
0.7877	Intermediate Similarity	NPC136860
0.7877	Intermediate Similarity	NPC476567
0.7877	Intermediate Similarity	NPC128019
0.7852	Intermediate Similarity	NPC130941
0.7832	Intermediate Similarity	NPC167944
0.7832	Intermediate Similarity	NPC231884
0.7832	Intermediate Similarity	NPC42793
0.7794	Intermediate Similarity	NPC298486
0.7786	Intermediate Similarity	NPC160193
0.7785	Intermediate Similarity	NPC106295
0.7785	Intermediate Similarity	NPC16107
0.7785	Intermediate Similarity	NPC51957
0.7785	Intermediate Similarity	NPC476144
0.7785	Intermediate Similarity	NPC210437
0.7778	Intermediate Similarity	NPC78733
0.777	Intermediate Similarity	NPC185838
0.7763	Intermediate Similarity	NPC26601
0.7733	Intermediate Similarity	NPC135538
0.7733	Intermediate Similarity	NPC24233
0.7733	Intermediate Similarity	NPC476571
0.7733	Intermediate Similarity	NPC246587
0.7733	Intermediate Similarity	NPC7467
0.7733	Intermediate Similarity	NPC428
0.7733	Intermediate Similarity	NPC147390
0.7727	Intermediate Similarity	NPC147091
0.7697	Intermediate Similarity	NPC476568
0.7667	Intermediate Similarity	NPC191376
0.7667	Intermediate Similarity	NPC144863
0.7667	Intermediate Similarity	NPC179825
0.7667	Intermediate Similarity	NPC476151
0.7667	Intermediate Similarity	NPC321505
0.7662	Intermediate Similarity	NPC41178
0.7662	Intermediate Similarity	NPC216459
0.7662	Intermediate Similarity	NPC76079
0.7662	Intermediate Similarity	NPC244112
0.7662	Intermediate Similarity	NPC138487
0.7662	Intermediate Similarity	NPC93593
0.7655	Intermediate Similarity	NPC248505
0.7655	Intermediate Similarity	NPC252107
0.7655	Intermediate Similarity	NPC95366
0.7647	Intermediate Similarity	NPC148898
0.7647	Intermediate Similarity	NPC233029
0.7647	Intermediate Similarity	NPC210148
0.7632	Intermediate Similarity	NPC274026
0.7613	Intermediate Similarity	NPC180756
0.7613	Intermediate Similarity	NPC146288
0.7613	Intermediate Similarity	NPC323443
0.7612	Intermediate Similarity	NPC120075
0.7606	Intermediate Similarity	NPC476570
0.7594	Intermediate Similarity	NPC47194
0.7586	Intermediate Similarity	NPC145446
0.7586	Intermediate Similarity	NPC137172
0.7586	Intermediate Similarity	NPC7018
0.7586	Intermediate Similarity	NPC99078
0.7582	Intermediate Similarity	NPC476579
0.7582	Intermediate Similarity	NPC8337
0.7582	Intermediate Similarity	NPC85747
0.758	Intermediate Similarity	NPC4304
0.758	Intermediate Similarity	NPC205167
0.7571	Intermediate Similarity	NPC301713
0.7566	Intermediate Similarity	NPC103379
0.7566	Intermediate Similarity	NPC92541
0.7566	Intermediate Similarity	NPC477565
0.7534	Intermediate Similarity	NPC253429
0.7534	Intermediate Similarity	NPC220923
0.7534	Intermediate Similarity	NPC470707
0.7533	Intermediate Similarity	NPC145304
0.7532	Intermediate Similarity	NPC133011
0.7532	Intermediate Similarity	NPC82285
0.7532	Intermediate Similarity	NPC476580
0.7531	Intermediate Similarity	NPC10871
0.7517	Intermediate Similarity	NPC96406
0.7517	Intermediate Similarity	NPC205178
0.7517	Intermediate Similarity	NPC277042
0.7517	Intermediate Similarity	NPC196609
0.7517	Intermediate Similarity	NPC251454
0.7517	Intermediate Similarity	NPC73883
0.7517	Intermediate Similarity	NPC136330
0.7517	Intermediate Similarity	NPC255817
0.7517	Intermediate Similarity	NPC230698
0.7516	Intermediate Similarity	NPC223125
0.7516	Intermediate Similarity	NPC97221
0.7516	Intermediate Similarity	NPC151895
0.7516	Intermediate Similarity	NPC88249
0.7516	Intermediate Similarity	NPC192768
0.7516	Intermediate Similarity	NPC220858
0.75	Intermediate Similarity	NPC31311
0.75	Intermediate Similarity	NPC323204
0.75	Intermediate Similarity	NPC234392
0.75	Intermediate Similarity	NPC186063
0.7484	Intermediate Similarity	NPC233650
0.7484	Intermediate Similarity	NPC218614
0.7483	Intermediate Similarity	NPC231572
0.7483	Intermediate Similarity	NPC114102
0.7468	Intermediate Similarity	NPC97072
0.7468	Intermediate Similarity	NPC249274
0.7468	Intermediate Similarity	NPC326316
0.7468	Intermediate Similarity	NPC215829
0.7468	Intermediate Similarity	NPC81733
0.7464	Intermediate Similarity	NPC211992
0.7455	Intermediate Similarity	NPC477560
0.7453	Intermediate Similarity	NPC301189
0.7453	Intermediate Similarity	NPC298186
0.7451	Intermediate Similarity	NPC207824
0.7451	Intermediate Similarity	NPC211296
0.7451	Intermediate Similarity	NPC60538
0.7448	Intermediate Similarity	NPC328419
0.7448	Intermediate Similarity	NPC167096
0.7448	Intermediate Similarity	NPC94280
0.7448	Intermediate Similarity	NPC159150
0.7448	Intermediate Similarity	NPC103947
0.7448	Intermediate Similarity	NPC45783
0.7448	Intermediate Similarity	NPC193673
0.7445	Intermediate Similarity	NPC321133
0.7444	Intermediate Similarity	NPC165106
0.7438	Intermediate Similarity	NPC180306
0.7438	Intermediate Similarity	NPC134858
0.7436	Intermediate Similarity	NPC2413
0.7436	Intermediate Similarity	NPC204828
0.7436	Intermediate Similarity	NPC469817
0.7436	Intermediate Similarity	NPC184026
0.7436	Intermediate Similarity	NPC172765
0.7436	Intermediate Similarity	NPC189266
0.7436	Intermediate Similarity	NPC278799
0.7436	Intermediate Similarity	NPC207757
0.7436	Intermediate Similarity	NPC110416
0.7436	Intermediate Similarity	NPC249797
0.7436	Intermediate Similarity	NPC39701
0.7436	Intermediate Similarity	NPC193949
0.7436	Intermediate Similarity	NPC295691
0.7436	Intermediate Similarity	NPC276588
0.7436	Intermediate Similarity	NPC5238
0.7436	Intermediate Similarity	NPC54379
0.7436	Intermediate Similarity	NPC127674
0.7431	Intermediate Similarity	NPC318862
0.7431	Intermediate Similarity	NPC214869
0.7419	Intermediate Similarity	NPC223124
0.7415	Intermediate Similarity	NPC113236
0.7415	Intermediate Similarity	NPC28641
0.7415	Intermediate Similarity	NPC194359
0.7415	Intermediate Similarity	NPC214036
0.7415	Intermediate Similarity	NPC225745
0.7413	Intermediate Similarity	NPC195749
0.7413	Intermediate Similarity	NPC470706
0.7413	Intermediate Similarity	NPC35961
0.7413	Intermediate Similarity	NPC52029
0.7407	Intermediate Similarity	NPC266176
0.7407	Intermediate Similarity	NPC158148
0.7407	Intermediate Similarity	NPC290759
0.7407	Intermediate Similarity	NPC82533
0.7405	Intermediate Similarity	NPC216816
0.7405	Intermediate Similarity	NPC106786
0.7405	Intermediate Similarity	NPC59028
0.7405	Intermediate Similarity	NPC118804
0.7405	Intermediate Similarity	NPC92191
0.7405	Intermediate Similarity	NPC111485
0.7397	Intermediate Similarity	NPC180647
0.7394	Intermediate Similarity	NPC153990
0.7389	Intermediate Similarity	NPC25084
0.7389	Intermediate Similarity	NPC247639
0.7389	Intermediate Similarity	NPC57512
0.7379	Intermediate Similarity	NPC160692
0.7379	Intermediate Similarity	NPC325568
0.7375	Intermediate Similarity	NPC476569
0.7375	Intermediate Similarity	NPC59567
0.7362	Intermediate Similarity	NPC75958
0.7358	Intermediate Similarity	NPC160298
0.7358	Intermediate Similarity	NPC266753
0.7358	Intermediate Similarity	NPC306902
0.7358	Intermediate Similarity	NPC477559
0.7358	Intermediate Similarity	NPC232924
0.7355	Intermediate Similarity	NPC76213
0.7355	Intermediate Similarity	NPC277669
0.7347	Intermediate Similarity	NPC301050

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 NPC475828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	699
0.2-0.3	976
0.3-0.4	2058
0.4-0.5	2756
0.5-0.6	1645
0.6-0.7	696
0.7-0.8	128
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8112	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5718	Phase 2
0.7971	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4236	Phase 3
0.7931	Intermediate Similarity	NPD4237	Approved
0.7832	Intermediate Similarity	NPD6895	Approved
0.7832	Intermediate Similarity	NPD6896	Approved
0.7785	Intermediate Similarity	NPD4584	Approved
0.7703	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5241	Discontinued
0.7533	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2492	Phase 1
0.7468	Intermediate Similarity	NPD4017	Approved
0.7467	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3640	Phase 3
0.7451	Intermediate Similarity	NPD3641	Approved
0.7451	Intermediate Similarity	NPD3639	Approved
0.7445	Intermediate Similarity	NPD2668	Approved
0.7445	Intermediate Similarity	NPD2667	Approved
0.7444	Intermediate Similarity	NPD5283	Phase 1
0.7417	Intermediate Similarity	NPD7124	Phase 2
0.7403	Intermediate Similarity	NPD4210	Discontinued
0.74	Intermediate Similarity	NPD6331	Phase 2
0.7389	Intermediate Similarity	NPD5772	Approved
0.7389	Intermediate Similarity	NPD5773	Approved
0.7379	Intermediate Similarity	NPD3110	Approved
0.7379	Intermediate Similarity	NPD3109	Approved
0.7347	Intermediate Similarity	NPD6111	Discontinued
0.7338	Intermediate Similarity	NPD6031	Approved
0.7338	Intermediate Similarity	NPD6030	Approved
0.7333	Intermediate Similarity	NPD5177	Phase 3
0.7333	Intermediate Similarity	NPD3060	Approved
0.7333	Intermediate Similarity	NPD4162	Approved
0.7325	Intermediate Similarity	NPD7298	Approved
0.731	Intermediate Similarity	NPD2674	Phase 3
0.7279	Intermediate Similarity	NPD2653	Approved
0.7278	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2040	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4772	Phase 2
0.7261	Intermediate Similarity	NPD4773	Phase 2
0.7255	Intermediate Similarity	NPD5297	Approved
0.7241	Intermediate Similarity	NPD1039	Discontinued
0.7234	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2563	Approved
0.7233	Intermediate Similarity	NPD2560	Approved
0.7208	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7018	Phase 2
0.7203	Intermediate Similarity	NPD7905	Discontinued
0.7195	Intermediate Similarity	NPD4481	Phase 3
0.7188	Intermediate Similarity	NPD6788	Approved
0.7183	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4166	Phase 2
0.717	Intermediate Similarity	NPD2978	Approved
0.717	Intermediate Similarity	NPD2977	Approved
0.7163	Intermediate Similarity	NPD2233	Approved
0.7163	Intermediate Similarity	NPD2232	Approved
0.7163	Intermediate Similarity	NPD2230	Approved
0.7152	Intermediate Similarity	NPD6385	Approved
0.7152	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6386	Approved
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7134	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2969	Approved
0.7134	Intermediate Similarity	NPD2970	Approved
0.7133	Intermediate Similarity	NPD2161	Phase 2
0.7125	Intermediate Similarity	NPD5978	Approved
0.7125	Intermediate Similarity	NPD5977	Approved
0.7123	Intermediate Similarity	NPD3144	Approved
0.7123	Intermediate Similarity	NPD3145	Approved
0.7115	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5976	Discontinued
0.7113	Intermediate Similarity	NPD1421	Approved
0.7113	Intermediate Similarity	NPD1420	Approved
0.7091	Intermediate Similarity	NPD2898	Approved
0.7091	Intermediate Similarity	NPD27	Approved
0.7091	Intermediate Similarity	NPD2489	Approved
0.7086	Intermediate Similarity	NPD1375	Discontinued
0.7075	Intermediate Similarity	NPD3532	Approved
0.7075	Intermediate Similarity	NPD4475	Approved
0.7075	Intermediate Similarity	NPD3530	Approved
0.7075	Intermediate Similarity	NPD4474	Approved
0.7075	Intermediate Similarity	NPD3531	Approved
0.7073	Intermediate Similarity	NPD3051	Approved
0.7073	Intermediate Similarity	NPD6071	Discontinued
0.7063	Intermediate Similarity	NPD2922	Phase 1
0.7059	Intermediate Similarity	NPD5754	Discontinued
0.7055	Intermediate Similarity	NPD5746	Approved
0.7055	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6873	Phase 2
0.7044	Intermediate Similarity	NPD7110	Phase 1
0.7044	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7831	Phase 2
0.7037	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7833	Phase 2
0.7032	Intermediate Similarity	NPD3124	Discontinued
0.7029	Intermediate Similarity	NPD3596	Phase 2
0.7012	Intermediate Similarity	NPD6107	Approved
0.7007	Intermediate Similarity	NPD5109	Approved
0.7007	Intermediate Similarity	NPD5110	Phase 2
0.7007	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD593	Approved
0.7007	Intermediate Similarity	NPD5111	Phase 2
0.7007	Intermediate Similarity	NPD595	Approved
0.7006	Intermediate Similarity	NPD2122	Discontinued
0.7	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1669	Approved
0.6987	Remote Similarity	NPD4123	Phase 3
0.6987	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1424	Approved
0.6981	Remote Similarity	NPD6876	Approved
0.6981	Remote Similarity	NPD6875	Approved
0.697	Remote Similarity	NPD4010	Discontinued
0.6966	Remote Similarity	NPD6584	Phase 3
0.6959	Remote Similarity	NPD7310	Approved
0.6959	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7311	Approved
0.6959	Remote Similarity	NPD5745	Approved
0.6959	Remote Similarity	NPD7312	Approved
0.6959	Remote Similarity	NPD7313	Approved
0.6929	Remote Similarity	NPD2486	Discontinued
0.6929	Remote Similarity	NPD6581	Approved
0.6929	Remote Similarity	NPD6580	Approved
0.6928	Remote Similarity	NPD7037	Approved
0.6928	Remote Similarity	NPD7153	Discontinued
0.6923	Remote Similarity	NPD1774	Approved
0.6919	Remote Similarity	NPD7309	Approved
0.6912	Remote Similarity	NPD228	Approved
0.6909	Remote Similarity	NPD7802	Discontinued
0.6905	Remote Similarity	NPD8251	Approved
0.6905	Remote Similarity	NPD8099	Discontinued
0.6905	Remote Similarity	NPD8252	Approved
0.6901	Remote Similarity	NPD3294	Phase 2
0.6897	Remote Similarity	NPD3053	Approved
0.6897	Remote Similarity	NPD4098	Discontinued
0.6897	Remote Similarity	NPD3055	Approved
0.6882	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2594	Approved
0.6879	Remote Similarity	NPD6382	Discontinued
0.6879	Remote Similarity	NPD2595	Approved
0.6879	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4739	Approved
0.6864	Remote Similarity	NPD8156	Discontinued
0.686	Remote Similarity	NPD7280	Phase 3
0.686	Remote Similarity	NPD7281	Phase 3
0.6857	Remote Similarity	NPD5536	Phase 2
0.6853	Remote Similarity	NPD3705	Approved
0.6839	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1350	Approved
0.6835	Remote Similarity	NPD1349	Approved
0.6835	Remote Similarity	NPD7526	Approved
0.6835	Remote Similarity	NPD52	Approved
0.6835	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1351	Approved
0.6831	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5604	Discontinued
0.6821	Remote Similarity	NPD2986	Phase 2
0.6821	Remote Similarity	NPD2989	Phase 2
0.6813	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2238	Phase 2
0.6792	Remote Similarity	NPD4727	Phase 1
0.6788	Remote Similarity	NPD4573	Approved
0.6788	Remote Similarity	NPD4571	Approved
0.6788	Remote Similarity	NPD4572	Approved
0.6781	Remote Similarity	NPD1818	Approved
0.6781	Remote Similarity	NPD1819	Approved
0.6781	Remote Similarity	NPD1820	Approved
0.6781	Remote Similarity	NPD1817	Approved
0.6776	Remote Similarity	NPD2200	Suspended
0.677	Remote Similarity	NPD4675	Approved
0.677	Remote Similarity	NPD4179	Approved
0.677	Remote Similarity	NPD4678	Approved
0.677	Remote Similarity	NPD4180	Approved
0.6765	Remote Similarity	NPD5312	Approved
0.6765	Remote Similarity	NPD5313	Approved
0.6761	Remote Similarity	NPD3443	Approved
0.6761	Remote Similarity	NPD3445	Approved
0.6761	Remote Similarity	NPD3444	Approved
0.6761	Remote Similarity	NPD4093	Discontinued
0.6759	Remote Similarity	NPD6542	Approved
0.6759	Remote Similarity	NPD6540	Phase 3
0.6759	Remote Similarity	NPD6543	Approved
0.6759	Remote Similarity	NPD6539	Approved
0.6759	Remote Similarity	NPD6582	Phase 2
0.6759	Remote Similarity	NPD6583	Phase 3
0.6753	Remote Similarity	NPD3656	Approved
0.6752	Remote Similarity	NPD2120	Phase 2
0.675	Remote Similarity	NPD3686	Approved
0.675	Remote Similarity	NPD3687	Approved
0.6748	Remote Similarity	NPD4585	Approved
0.6747	Remote Similarity	NPD2644	Approved
0.6746	Remote Similarity	NPD5966	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