NPASS Compound

Structure

NPC92191 OpenBabel07101718282D 23 26 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 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 -1.1590 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 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 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -2.6473 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -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 -0.0000 -1.0000 0.0000 C 0 0 2 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 1.2784 -3.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 1 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 1 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.15
Volume:	318.634
LogP:	0.594
LogD:	0.987
LogS:	-1.869
# Rotatable Bonds:	2
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.866
Synthetic Accessibility Score:	4.754
Fsp3:	0.444
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:	-5.242
MDCK Permeability:	2.082007995340973e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.361
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.951
Plasma Protein Binding (PPB):	39.88201904296875%
Volume Distribution (VD):	3.916
Pgp-substrate:	50.61690902709961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.68
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.378
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.941

ADMET: Excretion

Clearance (CL):	9.538
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.34
Human Hepatotoxicity (H-HT):	0.838
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.348
Carcinogencity:	0.923
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC92191

Natural Product ID:	NPC92191
*Common Name:**	(+)-11Alpha-Hydroxyerytravine
IUPAC Name:	(2R,9S,13bS)-11,12-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinoline-2,9-diol
Synonyms:	(+)-11Alpha-Hydroxyerytravine
Standard InCHIKey:	LRCYONYSPOTFTD-PNPHSEOMSA-N
Standard InCHI:	InChI=1S/C18H21NO4/c1-22-16-7-13-14(8-17(16)23-2)18-9-12(20)4-3-11(18)5-6-19(18)10-15(13)21/h3-5,7-8,12,15,20-21H,6,9-10H2,1-2H3/t12-,15+,18-/m0/s1
SMILES:	COc1cc2c(cc1OC)[C@H](O)CN1[C@@]32C[C@@H](O)C=CC3=CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218056
PubChem CID:	11695361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO11659	Erythrina mulungu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253849]
NPO11659	Erythrina mulungu	Species	Fabaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	158.5	n.a.	PMID[558159]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	27.7	n.a.	PMID[558159]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	126.56	n.a.	PMID[558159]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	22.44	n.a.	PMID[558159]

☑ 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 NPC92191 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	262
0.1-0.2	1271
0.2-0.3	5334
0.3-0.4	12389
0.4-0.5	5928
0.5-0.6	12467
0.6-0.7	4035
0.7-0.8	749
0.8-0.85	200
0.85-0.9	51
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59028
0.9527	High Similarity	NPC274026
0.9272	High Similarity	NPC82285
0.9272	High Similarity	NPC133011
0.9189	High Similarity	NPC130926
0.9062	High Similarity	NPC470739
0.9062	High Similarity	NPC477640
0.9062	High Similarity	NPC225597
0.9	High Similarity	NPC474475
0.8951	High Similarity	NPC49353
0.8938	High Similarity	NPC58766
0.8938	High Similarity	NPC290759
0.8938	High Similarity	NPC266176
0.8938	High Similarity	NPC475686
0.8938	High Similarity	NPC82533
0.8938	High Similarity	NPC158148
0.8917	High Similarity	NPC249274
0.8917	High Similarity	NPC205167
0.891	High Similarity	NPC475326
0.8889	High Similarity	NPC2314
0.8846	High Similarity	NPC147091
0.8774	High Similarity	NPC148898
0.8758	High Similarity	NPC150879
0.8758	High Similarity	NPC100566
0.8696	High Similarity	NPC476002
0.8684	High Similarity	NPC185838
0.8667	High Similarity	NPC474470
0.8642	High Similarity	NPC181653
0.8642	High Similarity	NPC190332
0.8636	High Similarity	NPC135538
0.8636	High Similarity	NPC24233
0.8636	High Similarity	NPC147390
0.8636	High Similarity	NPC476571
0.8636	High Similarity	NPC246587
0.8636	High Similarity	NPC428
0.8606	High Similarity	NPC187678
0.8571	High Similarity	NPC191376
0.8571	High Similarity	NPC233650
0.8571	High Similarity	NPC476151
0.8571	High Similarity	NPC320104
0.8571	High Similarity	NPC321505
0.8571	High Similarity	NPC179825
0.8563	High Similarity	NPC244554
0.8562	High Similarity	NPC4304
0.8562	High Similarity	NPC97072
0.8562	High Similarity	NPC215829
0.8543	High Similarity	NPC188163
0.8543	High Similarity	NPC328750
0.8543	High Similarity	NPC474915
0.8543	High Similarity	NPC213206
0.8528	High Similarity	NPC252960
0.8519	High Similarity	NPC134858
0.8519	High Similarity	NPC169743
0.8477	Intermediate Similarity	NPC314682
0.8462	Intermediate Similarity	NPC248642
0.8462	Intermediate Similarity	NPC103379
0.8462	Intermediate Similarity	NPC477565
0.8457	Intermediate Similarity	NPC218614
0.8443	Intermediate Similarity	NPC237044
0.8438	Intermediate Similarity	NPC148014
0.8438	Intermediate Similarity	NPC315707
0.8438	Intermediate Similarity	NPC40389
0.8438	Intermediate Similarity	NPC78359
0.8438	Intermediate Similarity	NPC65490
0.8428	Intermediate Similarity	NPC39701
0.8428	Intermediate Similarity	NPC207757
0.8428	Intermediate Similarity	NPC54379
0.8428	Intermediate Similarity	NPC110416
0.8428	Intermediate Similarity	NPC172765
0.8428	Intermediate Similarity	NPC189266
0.8428	Intermediate Similarity	NPC295691
0.8428	Intermediate Similarity	NPC5238
0.8428	Intermediate Similarity	NPC469817
0.8428	Intermediate Similarity	NPC249797
0.8428	Intermediate Similarity	NPC127674
0.8428	Intermediate Similarity	NPC193949
0.8428	Intermediate Similarity	NPC2413
0.8428	Intermediate Similarity	NPC276588
0.8428	Intermediate Similarity	NPC278799
0.8428	Intermediate Similarity	NPC204828
0.8428	Intermediate Similarity	NPC184026
0.8415	Intermediate Similarity	NPC210140
0.8412	Intermediate Similarity	NPC156576
0.8408	Intermediate Similarity	NPC151895
0.8408	Intermediate Similarity	NPC192768
0.8408	Intermediate Similarity	NPC88249
0.8408	Intermediate Similarity	NPC97221
0.8408	Intermediate Similarity	NPC220858
0.8405	Intermediate Similarity	NPC231198
0.8393	Intermediate Similarity	NPC474325
0.8383	Intermediate Similarity	NPC304675
0.8375	Intermediate Similarity	NPC160931
0.8375	Intermediate Similarity	NPC37205
0.8364	Intermediate Similarity	NPC160570
0.8354	Intermediate Similarity	NPC13916
0.8354	Intermediate Similarity	NPC264850
0.8353	Intermediate Similarity	NPC233718
0.8344	Intermediate Similarity	NPC207824
0.8344	Intermediate Similarity	NPC60538
0.8343	Intermediate Similarity	NPC474745
0.8343	Intermediate Similarity	NPC126284
0.8333	Intermediate Similarity	NPC51957
0.8333	Intermediate Similarity	NPC106295
0.8333	Intermediate Similarity	NPC16107
0.8333	Intermediate Similarity	NPC210437
0.8333	Intermediate Similarity	NPC476144
0.8313	Intermediate Similarity	NPC311991
0.8313	Intermediate Similarity	NPC78733
0.8312	Intermediate Similarity	NPC136860
0.8312	Intermediate Similarity	NPC476567
0.8312	Intermediate Similarity	NPC128019
0.8303	Intermediate Similarity	NPC117188
0.8303	Intermediate Similarity	NPC158376
0.8303	Intermediate Similarity	NPC12053
0.8303	Intermediate Similarity	NPC205421
0.8303	Intermediate Similarity	NPC306555
0.8303	Intermediate Similarity	NPC145832
0.8303	Intermediate Similarity	NPC474931
0.8303	Intermediate Similarity	NPC81218
0.8293	Intermediate Similarity	NPC247972
0.8293	Intermediate Similarity	NPC24465
0.8284	Intermediate Similarity	NPC294790
0.8284	Intermediate Similarity	NPC118633
0.8284	Intermediate Similarity	NPC148693
0.8282	Intermediate Similarity	NPC60186
0.828	Intermediate Similarity	NPC7467
0.828	Intermediate Similarity	NPC475959
0.8278	Intermediate Similarity	NPC131204
0.8278	Intermediate Similarity	NPC301050
0.8253	Intermediate Similarity	NPC83198
0.8253	Intermediate Similarity	NPC204908
0.8243	Intermediate Similarity	NPC160193
0.8242	Intermediate Similarity	NPC124657
0.8239	Intermediate Similarity	NPC277669
0.8239	Intermediate Similarity	NPC76213
0.8225	Intermediate Similarity	NPC241704
0.8221	Intermediate Similarity	NPC18402
0.8214	Intermediate Similarity	NPC232386
0.8214	Intermediate Similarity	NPC190783
0.8214	Intermediate Similarity	NPC152680
0.821	Intermediate Similarity	NPC129603
0.821	Intermediate Similarity	NPC476572
0.8204	Intermediate Similarity	NPC75958
0.8204	Intermediate Similarity	NPC329911
0.8198	Intermediate Similarity	NPC475981
0.8198	Intermediate Similarity	NPC474746
0.8193	Intermediate Similarity	NPC474324
0.8193	Intermediate Similarity	NPC57812
0.8187	Intermediate Similarity	NPC37272
0.8182	Intermediate Similarity	NPC232514
0.8182	Intermediate Similarity	NPC136508
0.8182	Intermediate Similarity	NPC253043
0.8182	Intermediate Similarity	NPC477563
0.8182	Intermediate Similarity	NPC306843
0.8182	Intermediate Similarity	NPC276944
0.8182	Intermediate Similarity	NPC76116
0.8182	Intermediate Similarity	NPC78222
0.8182	Intermediate Similarity	NPC196447
0.8182	Intermediate Similarity	NPC212794
0.8182	Intermediate Similarity	NPC238530
0.8182	Intermediate Similarity	NPC13504
0.8182	Intermediate Similarity	NPC96603
0.816	Intermediate Similarity	NPC111485
0.8155	Intermediate Similarity	NPC57272
0.8148	Intermediate Similarity	NPC323443
0.8148	Intermediate Similarity	NPC180756
0.8144	Intermediate Similarity	NPC475845
0.8137	Intermediate Similarity	NPC2295
0.8137	Intermediate Similarity	NPC477564
0.8129	Intermediate Similarity	NPC99179
0.8129	Intermediate Similarity	NPC32154
0.8125	Intermediate Similarity	NPC476579
0.8121	Intermediate Similarity	NPC124433
0.8121	Intermediate Similarity	NPC293871
0.8121	Intermediate Similarity	NPC1229
0.8121	Intermediate Similarity	NPC324144
0.8103	Intermediate Similarity	NPC214116
0.8103	Intermediate Similarity	NPC230098
0.8095	Intermediate Similarity	NPC474708
0.8086	Intermediate Similarity	NPC99659
0.8086	Intermediate Similarity	NPC325871
0.8086	Intermediate Similarity	NPC41178
0.8086	Intermediate Similarity	NPC216459
0.8086	Intermediate Similarity	NPC138487
0.807	Intermediate Similarity	NPC320223
0.807	Intermediate Similarity	NPC15919
0.807	Intermediate Similarity	NPC114364
0.8047	Intermediate Similarity	NPC476331
0.8046	Intermediate Similarity	NPC9867
0.8037	Intermediate Similarity	NPC146288
0.8036	Intermediate Similarity	NPC164429
0.8025	Intermediate Similarity	NPC294249
0.8012	Intermediate Similarity	NPC59567
0.8	Intermediate Similarity	NPC66341
0.8	Intermediate Similarity	NPC192135
0.8	Intermediate Similarity	NPC27410
0.8	Intermediate Similarity	NPC166014
0.8	Intermediate Similarity	NPC477020
0.7988	Intermediate Similarity	NPC109925
0.7987	Intermediate Similarity	NPC253429

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 NPC92191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	651
0.2-0.3	990
0.3-0.4	2117
0.4-0.5	2646
0.5-0.6	1709
0.6-0.7	677
0.7-0.8	181
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8608	High Similarity	NPD6818	Clinical (unspecified phase)
0.8543	High Similarity	NPD4664	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD4773	Phase 2
0.8481	Intermediate Similarity	NPD4772	Phase 2
0.8466	Intermediate Similarity	NPD6071	Discontinued
0.8438	Intermediate Similarity	NPD2560	Approved
0.8438	Intermediate Similarity	NPD2563	Approved
0.8377	Intermediate Similarity	NPD5241	Discontinued
0.8333	Intermediate Similarity	NPD4584	Approved
0.8193	Intermediate Similarity	NPD2970	Approved
0.8193	Intermediate Similarity	NPD2969	Approved
0.8129	Intermediate Similarity	NPD4236	Phase 3
0.8129	Intermediate Similarity	NPD4237	Approved
0.8037	Intermediate Similarity	NPD5773	Approved
0.8037	Intermediate Similarity	NPD5772	Approved
0.8036	Intermediate Similarity	NPD27	Approved
0.8036	Intermediate Similarity	NPD2489	Approved
0.8025	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3051	Approved
0.8013	Intermediate Similarity	NPD3060	Approved
0.8012	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2898	Approved
0.7901	Intermediate Similarity	NPD4017	Approved
0.7898	Intermediate Similarity	NPD7906	Approved
0.7888	Intermediate Similarity	NPD3639	Approved
0.7888	Intermediate Similarity	NPD6031	Approved
0.7888	Intermediate Similarity	NPD6030	Approved
0.7888	Intermediate Similarity	NPD3641	Approved
0.7888	Intermediate Similarity	NPD3640	Phase 3
0.7875	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6107	Approved
0.7841	Intermediate Similarity	NPD4663	Approved
0.7829	Intermediate Similarity	NPD8053	Approved
0.7829	Intermediate Similarity	NPD8054	Approved
0.7818	Intermediate Similarity	NPD2978	Approved
0.7818	Intermediate Similarity	NPD2977	Approved
0.7811	Intermediate Similarity	NPD4010	Discontinued
0.7791	Intermediate Similarity	NPD8156	Discontinued
0.7785	Intermediate Similarity	NPD5177	Phase 3
0.7784	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7831	Phase 2
0.7784	Intermediate Similarity	NPD7833	Phase 2
0.7771	Intermediate Similarity	NPD7313	Approved
0.7771	Intermediate Similarity	NPD7311	Approved
0.7771	Intermediate Similarity	NPD7310	Approved
0.7771	Intermediate Similarity	NPD4577	Approved
0.7771	Intermediate Similarity	NPD4578	Approved
0.7771	Intermediate Similarity	NPD7312	Approved
0.7764	Intermediate Similarity	NPD4123	Phase 3
0.7763	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7298	Approved
0.7733	Intermediate Similarity	NPD8099	Discontinued
0.7733	Intermediate Similarity	NPD8251	Approved
0.7733	Intermediate Similarity	NPD8252	Approved
0.7727	Intermediate Similarity	NPD7309	Approved
0.7727	Intermediate Similarity	NPD2238	Phase 2
0.7719	Intermediate Similarity	NPD4481	Phase 3
0.7688	Intermediate Similarity	NPD2677	Approved
0.7673	Intermediate Similarity	NPD4162	Approved
0.7658	Intermediate Similarity	NPD1375	Discontinued
0.7643	Intermediate Similarity	NPD1753	Discontinued
0.764	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4210	Discontinued
0.7622	Intermediate Similarity	NPD3687	Approved
0.7622	Intermediate Similarity	NPD3686	Approved
0.7619	Intermediate Similarity	NPD6788	Approved
0.76	Intermediate Similarity	NPD6297	Approved
0.7597	Intermediate Similarity	NPD5718	Phase 2
0.7576	Intermediate Similarity	NPD4005	Discontinued
0.7546	Intermediate Similarity	NPD1424	Approved
0.7541	Intermediate Similarity	NPD5582	Discontinued
0.7541	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4675	Approved
0.753	Intermediate Similarity	NPD4678	Approved
0.7528	Intermediate Similarity	NPD6853	Approved
0.7528	Intermediate Similarity	NPD6851	Approved
0.7516	Intermediate Similarity	NPD817	Approved
0.7516	Intermediate Similarity	NPD823	Approved
0.7515	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5313	Approved
0.7486	Intermediate Similarity	NPD5312	Approved
0.7484	Intermediate Similarity	NPD2161	Phase 2
0.747	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3692	Discontinued
0.7468	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4420	Approved
0.7436	Intermediate Similarity	NPD2674	Phase 3
0.7405	Intermediate Similarity	NPD2973	Approved
0.7405	Intermediate Similarity	NPD2974	Approved
0.7405	Intermediate Similarity	NPD2975	Approved
0.7399	Intermediate Similarity	NPD4166	Phase 2
0.7394	Intermediate Similarity	NPD6090	Discontinued
0.7394	Intermediate Similarity	NPD5006	Approved
0.7394	Intermediate Similarity	NPD5005	Approved
0.7386	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4103	Phase 2
0.7384	Intermediate Similarity	NPD5677	Discontinued
0.7378	Intermediate Similarity	NPD3124	Discontinued
0.7368	Intermediate Similarity	NPD5604	Discontinued
0.7358	Intermediate Similarity	NPD6896	Approved
0.7358	Intermediate Similarity	NPD6895	Approved
0.7356	Intermediate Similarity	NPD6688	Approved
0.7356	Intermediate Similarity	NPD6687	Approved
0.7349	Intermediate Similarity	NPD2122	Discontinued
0.7341	Intermediate Similarity	NPD7802	Discontinued
0.734	Intermediate Similarity	NPD3450	Approved
0.734	Intermediate Similarity	NPD3452	Approved
0.734	Intermediate Similarity	NPD2493	Approved
0.734	Intermediate Similarity	NPD2494	Approved
0.7329	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1130	Approved
0.7325	Intermediate Similarity	NPD1132	Approved
0.7325	Intermediate Similarity	NPD1136	Approved
0.7317	Intermediate Similarity	NPD3122	Phase 3
0.7317	Intermediate Similarity	NPD7124	Phase 2
0.7303	Intermediate Similarity	NPD2232	Approved
0.7303	Intermediate Similarity	NPD2230	Approved
0.7303	Intermediate Similarity	NPD2233	Approved
0.7289	Intermediate Similarity	NPD7526	Approved
0.7289	Intermediate Similarity	NPD52	Approved
0.7289	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4580	Approved
0.7278	Intermediate Similarity	NPD3061	Approved
0.7278	Intermediate Similarity	NPD3059	Approved
0.7278	Intermediate Similarity	NPD3062	Approved
0.7273	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1774	Approved
0.7273	Intermediate Similarity	NPD2420	Approved
0.7273	Intermediate Similarity	NPD2421	Approved
0.7268	Intermediate Similarity	NPD2845	Phase 2
0.7268	Intermediate Similarity	NPD2843	Phase 2
0.7267	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4055	Discovery
0.7263	Intermediate Similarity	NPD7039	Approved
0.7263	Intermediate Similarity	NPD7038	Approved
0.7261	Intermediate Similarity	NPD601	Approved
0.7261	Intermediate Similarity	NPD597	Approved
0.7261	Intermediate Similarity	NPD598	Approved
0.7261	Intermediate Similarity	NPD3144	Approved
0.7261	Intermediate Similarity	NPD3145	Approved
0.7256	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4659	Approved
0.7251	Intermediate Similarity	NPD5978	Approved
0.7251	Intermediate Similarity	NPD5977	Approved
0.7246	Intermediate Similarity	NPD5976	Discontinued
0.7229	Intermediate Similarity	NPD3157	Approved
0.7229	Intermediate Similarity	NPD3158	Phase 1
0.7228	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD2490	Approved
0.7228	Intermediate Similarity	NPD2488	Approved
0.7225	Intermediate Similarity	NPD4582	Approved
0.7225	Intermediate Similarity	NPD4583	Approved
0.7222	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2667	Approved
0.7219	Intermediate Similarity	NPD2668	Approved
0.7213	Intermediate Similarity	NPD4157	Discontinued
0.7212	Intermediate Similarity	NPD3845	Phase 1
0.7195	Intermediate Similarity	NPD6331	Phase 2
0.7195	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6042	Phase 2
0.7191	Intermediate Similarity	NPD42	Phase 2
0.7189	Intermediate Similarity	NPD7296	Approved
0.7188	Intermediate Similarity	NPD5314	Approved
0.7184	Intermediate Similarity	NPD2904	Discontinued
0.7182	Intermediate Similarity	NPD2971	Approved
0.7182	Intermediate Similarity	NPD2968	Approved
0.7178	Intermediate Similarity	NPD7153	Discontinued
0.7173	Intermediate Similarity	NPD4002	Approved
0.7173	Intermediate Similarity	NPD4004	Approved
0.7168	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5242	Approved
0.7152	Intermediate Similarity	NPD5160	Discontinued
0.7135	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5709	Phase 3
0.712	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3656	Approved
0.7115	Intermediate Similarity	NPD9621	Approved
0.7115	Intermediate Similarity	NPD9619	Approved
0.7115	Intermediate Similarity	NPD9620	Approved
0.7111	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3531	Approved
0.7107	Intermediate Similarity	NPD4475	Approved
0.7107	Intermediate Similarity	NPD3532	Approved
0.7107	Intermediate Similarity	NPD3530	Approved
0.7107	Intermediate Similarity	NPD4474	Approved
0.7105	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3179	Approved
0.7089	Intermediate Similarity	NPD3027	Phase 3
0.7089	Intermediate Similarity	NPD3180	Approved
0.7088	Intermediate Similarity	NPD7281	Phase 3
0.7088	Intermediate Similarity	NPD7280	Phase 3
0.7088	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4666	Phase 3
0.7083	Intermediate Similarity	NPD5261	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