NPASS Compound

Structure

CID234078 OpenBabel06191716032D 26 30 0 0 1 0 0 0 0 0999 V2000 5.0737 0.9433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1219 2.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5162 -0.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6779 -1.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6775 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6777 -1.9376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 0.9679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3551 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.9040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1941 1.4514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8388 -1.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 -1.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5170 1.4519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3554 0.9675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5172 2.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8386 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8389 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6376 2.9283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 2.5165 -0.4847 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6379 3.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7577 2.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1943 2.4197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 26 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 10 1 1 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 M CHG 1 22 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.15
Volume:	356.262
LogP:	4.199
LogD:	3.674
LogS:	-4.856
# Rotatable Bonds:	2
TPSA:	53.35
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	4.055
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.679
MDCK Permeability:	3.867204213747755e-05
Pgp-inhibitor:	0.049
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.849
30% Bioavailability (F30%):	0.653

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	90.7822036743164%
Volume Distribution (VD):	0.848
Pgp-substrate:	5.445634365081787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.896
CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.552

ADMET: Excretion

Clearance (CL):	6.96
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.64
Human Hepatotoxicity (H-HT):	0.928
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.985
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.25
Carcinogencity:	0.973
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC234078

Natural Product ID:	NPC234078
*Common Name:**	WYTGDNHDOZPMIW-VBNZEHGJSA-O
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WYTGDNHDOZPMIW-VBNZEHGJSA-O
Standard InCHI:	InChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/p+1/t12-,15-,16+/m0/s1
SMILES:	COC(=O)C1=CO[C@H]([C@@H]2[C@@H]1Cc1n(C2)ccc2=c3c(=[NH+]c12)cccc3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3559488
PubChem CID:	88100948 73391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7282	Rauvolfia serpentina	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
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	2200.0	nM	PMID[453428]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Ratio IC50	=	10.0	n.a.	PMID[453429]

☑ 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 NPC234078 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	323
0.1-0.2	2071
0.2-0.3	11190
0.3-0.4	19444
0.4-0.5	5236
0.5-0.6	1971
0.6-0.7	2077
0.7-0.8	350
0.8-0.85	24
0.85-0.9	6
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221100
0.963	High Similarity	NPC238457
0.9263	High Similarity	NPC199851
0.9263	High Similarity	NPC128265
0.9263	High Similarity	NPC312870
0.9263	High Similarity	NPC254240
0.9263	High Similarity	NPC294909
0.8737	High Similarity	NPC63199
0.8737	High Similarity	NPC196251
0.8737	High Similarity	NPC111602
0.8737	High Similarity	NPC102338
0.8594	High Similarity	NPC472112
0.8469	Intermediate Similarity	NPC245916
0.8418	Intermediate Similarity	NPC220151
0.8418	Intermediate Similarity	NPC19692
0.841	Intermediate Similarity	NPC472113
0.8333	Intermediate Similarity	NPC258480
0.8302	Intermediate Similarity	NPC21638
0.8247	Intermediate Similarity	NPC62749
0.819	Intermediate Similarity	NPC82070
0.8154	Intermediate Similarity	NPC66210
0.8152	Intermediate Similarity	NPC52254
0.8125	Intermediate Similarity	NPC118940
0.8071	Intermediate Similarity	NPC175474
0.8009	Intermediate Similarity	NPC476114
0.8	Intermediate Similarity	NPC475271
0.7941	Intermediate Similarity	NPC49196
0.7941	Intermediate Similarity	NPC313985
0.7941	Intermediate Similarity	NPC195461
0.7941	Intermediate Similarity	NPC81654
0.7941	Intermediate Similarity	NPC249150
0.7941	Intermediate Similarity	NPC79129
0.7936	Intermediate Similarity	NPC33949
0.7931	Intermediate Similarity	NPC52557
0.7925	Intermediate Similarity	NPC148183
0.7925	Intermediate Similarity	NPC152768
0.7919	Intermediate Similarity	NPC472107
0.7919	Intermediate Similarity	NPC79062
0.7907	Intermediate Similarity	NPC60621
0.79	Intermediate Similarity	NPC472097
0.7868	Intermediate Similarity	NPC472119
0.786	Intermediate Similarity	NPC472099
0.785	Intermediate Similarity	NPC174788
0.7843	Intermediate Similarity	NPC50503
0.7839	Intermediate Similarity	NPC472323
0.7817	Intermediate Similarity	NPC143533
0.7808	Intermediate Similarity	NPC476491
0.7806	Intermediate Similarity	NPC15840
0.7803	Intermediate Similarity	NPC57453
0.7773	Intermediate Similarity	NPC123839
0.7767	Intermediate Similarity	NPC281049
0.7762	Intermediate Similarity	NPC266249
0.7756	Intermediate Similarity	NPC67288
0.7727	Intermediate Similarity	NPC139291
0.7727	Intermediate Similarity	NPC472108
0.7727	Intermediate Similarity	NPC472104
0.7727	Intermediate Similarity	NPC475258
0.7718	Intermediate Similarity	NPC74413
0.7716	Intermediate Similarity	NPC469896
0.7714	Intermediate Similarity	NPC474905
0.771	Intermediate Similarity	NPC477979
0.7704	Intermediate Similarity	NPC14113
0.7704	Intermediate Similarity	NPC145885
0.7704	Intermediate Similarity	NPC84827
0.7704	Intermediate Similarity	NPC234987
0.7692	Intermediate Similarity	NPC260900
0.7685	Intermediate Similarity	NPC55493
0.7677	Intermediate Similarity	NPC71037
0.7667	Intermediate Similarity	NPC472064
0.7659	Intermediate Similarity	NPC79356
0.7659	Intermediate Similarity	NPC102592
0.7647	Intermediate Similarity	NPC472295
0.7647	Intermediate Similarity	NPC472210
0.7647	Intermediate Similarity	NPC247735
0.7647	Intermediate Similarity	NPC81802
0.7647	Intermediate Similarity	NPC269886
0.7644	Intermediate Similarity	NPC477549
0.7638	Intermediate Similarity	NPC472109
0.7638	Intermediate Similarity	NPC472110
0.7617	Intermediate Similarity	NPC56233
0.7614	Intermediate Similarity	NPC326575
0.7612	Intermediate Similarity	NPC235684
0.7608	Intermediate Similarity	NPC476874
0.7608	Intermediate Similarity	NPC57398
0.7606	Intermediate Similarity	NPC167860
0.7606	Intermediate Similarity	NPC123976
0.7604	Intermediate Similarity	NPC473310
0.7604	Intermediate Similarity	NPC21174
0.7604	Intermediate Similarity	NPC271797
0.7602	Intermediate Similarity	NPC909
0.7602	Intermediate Similarity	NPC475338
0.7602	Intermediate Similarity	NPC472762
0.76	Intermediate Similarity	NPC284678
0.7586	Intermediate Similarity	NPC314333
0.7581	Intermediate Similarity	NPC472291
0.7577	Intermediate Similarity	NPC78020
0.7573	Intermediate Similarity	NPC472116
0.7571	Intermediate Similarity	NPC476115
0.7571	Intermediate Similarity	NPC165599
0.7563	Intermediate Similarity	NPC267885
0.7561	Intermediate Similarity	NPC198673
0.7559	Intermediate Similarity	NPC472070
0.7559	Intermediate Similarity	NPC478158
0.7558	Intermediate Similarity	NPC312645
0.7548	Intermediate Similarity	NPC81535
0.7545	Intermediate Similarity	NPC260434
0.7537	Intermediate Similarity	NPC321708
0.7536	Intermediate Similarity	NPC132539
0.7536	Intermediate Similarity	NPC227582
0.7535	Intermediate Similarity	NPC264176
0.7525	Intermediate Similarity	NPC315555
0.7525	Intermediate Similarity	NPC111275
0.7524	Intermediate Similarity	NPC472069
0.7524	Intermediate Similarity	NPC472062
0.7524	Intermediate Similarity	NPC472063
0.7522	Intermediate Similarity	NPC182222
0.7513	Intermediate Similarity	NPC110500
0.7513	Intermediate Similarity	NPC149155
0.7513	Intermediate Similarity	NPC203468
0.7512	Intermediate Similarity	NPC472292
0.7511	Intermediate Similarity	NPC122436
0.7511	Intermediate Similarity	NPC148889
0.7511	Intermediate Similarity	NPC229893
0.7511	Intermediate Similarity	NPC469554
0.75	Intermediate Similarity	NPC472065
0.75	Intermediate Similarity	NPC474916
0.75	Intermediate Similarity	NPC113626
0.75	Intermediate Similarity	NPC89508
0.75	Intermediate Similarity	NPC329858
0.75	Intermediate Similarity	NPC168911
0.75	Intermediate Similarity	NPC471506
0.75	Intermediate Similarity	NPC191415
0.7488	Intermediate Similarity	NPC472293
0.7487	Intermediate Similarity	NPC219336
0.7487	Intermediate Similarity	NPC213468
0.7487	Intermediate Similarity	NPC126709
0.7487	Intermediate Similarity	NPC248041
0.7487	Intermediate Similarity	NPC55772
0.7478	Intermediate Similarity	NPC473105
0.7476	Intermediate Similarity	NPC232727
0.7475	Intermediate Similarity	NPC280290
0.7475	Intermediate Similarity	NPC472122
0.7475	Intermediate Similarity	NPC24594
0.7465	Intermediate Similarity	NPC478157
0.7465	Intermediate Similarity	NPC474412
0.7464	Intermediate Similarity	NPC472296
0.7464	Intermediate Similarity	NPC472297
0.7463	Intermediate Similarity	NPC102755
0.7463	Intermediate Similarity	NPC138370
0.7462	Intermediate Similarity	NPC472123
0.7458	Intermediate Similarity	NPC152620
0.7454	Intermediate Similarity	NPC472098
0.744	Intermediate Similarity	NPC202812
0.7438	Intermediate Similarity	NPC478077
0.7437	Intermediate Similarity	NPC217372
0.7437	Intermediate Similarity	NPC183662
0.7437	Intermediate Similarity	NPC15573
0.7431	Intermediate Similarity	NPC472027
0.7431	Intermediate Similarity	NPC36405
0.7429	Intermediate Similarity	NPC176538
0.7429	Intermediate Similarity	NPC252338
0.7429	Intermediate Similarity	NPC214428
0.7426	Intermediate Similarity	NPC228835
0.7426	Intermediate Similarity	NPC53534
0.7424	Intermediate Similarity	NPC101350
0.7423	Intermediate Similarity	NPC478182
0.7419	Intermediate Similarity	NPC229348
0.7416	Intermediate Similarity	NPC239954
0.7415	Intermediate Similarity	NPC469501
0.7415	Intermediate Similarity	NPC469470
0.7411	Intermediate Similarity	NPC476492
0.7409	Intermediate Similarity	NPC193267
0.7409	Intermediate Similarity	NPC213530
0.7406	Intermediate Similarity	NPC317701
0.7404	Intermediate Similarity	NPC473800
0.74	Intermediate Similarity	NPC12649
0.74	Intermediate Similarity	NPC283219
0.7395	Intermediate Similarity	NPC174672
0.7395	Intermediate Similarity	NPC174758
0.7385	Intermediate Similarity	NPC313640
0.7383	Intermediate Similarity	NPC244741
0.7383	Intermediate Similarity	NPC477065
0.7381	Intermediate Similarity	NPC284338
0.7381	Intermediate Similarity	NPC241024
0.738	Intermediate Similarity	NPC235685
0.7378	Intermediate Similarity	NPC314954
0.7376	Intermediate Similarity	NPC469358
0.7373	Intermediate Similarity	NPC318299
0.7373	Intermediate Similarity	NPC26679
0.7371	Intermediate Similarity	NPC327592
0.7371	Intermediate Similarity	NPC285558
0.7368	Intermediate Similarity	NPC106824
0.7368	Intermediate Similarity	NPC141454
0.7366	Intermediate Similarity	NPC24370
0.7366	Intermediate Similarity	NPC319232
0.7363	Intermediate Similarity	NPC187827
0.7363	Intermediate Similarity	NPC472105
0.7358	Intermediate Similarity	NPC193761
0.7358	Intermediate Similarity	NPC162730
0.7357	Intermediate Similarity	NPC475720

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 NPC234078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	599
0.2-0.3	841
0.3-0.4	1771
0.4-0.5	2770
0.5-0.6	2118
0.6-0.7	805
0.7-0.8	48
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9263	High Similarity	NPD4501	Approved
0.9263	High Similarity	NPD4500	Approved
0.7941	Intermediate Similarity	NPD4600	Approved
0.7941	Intermediate Similarity	NPD4601	Approved
0.784	Intermediate Similarity	NPD3393	Approved
0.784	Intermediate Similarity	NPD3394	Approved
0.784	Intermediate Similarity	NPD3389	Approved
0.7805	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2509	Approved
0.7762	Intermediate Similarity	NPD2510	Approved
0.7739	Intermediate Similarity	NPD5482	Discontinued
0.7688	Intermediate Similarity	NPD6178	Phase 3
0.7681	Intermediate Similarity	NPD6479	Discontinued
0.7656	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2095	Phase 2
0.7638	Intermediate Similarity	NPD2094	Phase 2
0.7638	Intermediate Similarity	NPD2092	Phase 2
0.7619	Intermediate Similarity	NPD5901	Discontinued
0.7608	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5072	Discontinued
0.76	Intermediate Similarity	NPD2091	Phase 2
0.76	Intermediate Similarity	NPD2096	Phase 2
0.7586	Intermediate Similarity	NPD4499	Approved
0.7563	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD482	Approved
0.75	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD6770	Approved
0.7488	Intermediate Similarity	NPD7470	Discontinued
0.7462	Intermediate Similarity	NPD750	Phase 2
0.7454	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5426	Phase 3
0.743	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5450	Discontinued
0.7418	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7957	Phase 1
0.7395	Intermediate Similarity	NPD4506	Discontinued
0.7385	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3947	Discontinued
0.7356	Intermediate Similarity	NPD4602	Approved
0.7349	Intermediate Similarity	NPD7665	Phase 2
0.7349	Intermediate Similarity	NPD7666	Phase 3
0.7333	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6176	Phase 1
0.7299	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6999	Discontinued
0.7297	Intermediate Similarity	NPD6242	Discontinued
0.7281	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3006	Discontinued
0.7261	Intermediate Similarity	NPD7708	Approved
0.7257	Intermediate Similarity	NPD6165	Phase 2
0.7257	Intermediate Similarity	NPD6164	Phase 2
0.7256	Intermediate Similarity	NPD7001	Phase 3
0.7248	Intermediate Similarity	NPD5475	Discontinued
0.7248	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4558	Phase 2
0.724	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7955	Approved
0.722	Intermediate Similarity	NPD7956	Approved
0.7214	Intermediate Similarity	NPD5104	Approved
0.7213	Intermediate Similarity	NPD7803	Approved
0.7209	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5003	Discontinued
0.719	Intermediate Similarity	NPD7944	Discontinued
0.7176	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7404	Approved
0.7171	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8072	Approved
0.7162	Intermediate Similarity	NPD8326	Phase 3
0.7162	Intermediate Similarity	NPD8325	Phase 3
0.7162	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2837	Discontinued
0.7143	Intermediate Similarity	NPD7850	Discontinued
0.7143	Intermediate Similarity	NPD7851	Phase 1
0.7136	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2336	Approved
0.7123	Intermediate Similarity	NPD2880	Discontinued
0.7121	Intermediate Similarity	NPD2915	Discontinued
0.7112	Intermediate Similarity	NPD5891	Approved
0.7109	Intermediate Similarity	NPD7619	Phase 3
0.7109	Intermediate Similarity	NPD7618	Phase 3
0.7108	Intermediate Similarity	NPD5899	Approved
0.7108	Intermediate Similarity	NPD5897	Approved
0.7108	Intermediate Similarity	NPD5898	Approved
0.7103	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7952	Approved
0.71	Intermediate Similarity	NPD7953	Approved
0.71	Intermediate Similarity	NPD7951	Approved
0.71	Intermediate Similarity	NPD7790	Approved
0.71	Intermediate Similarity	NPD7950	Approved
0.71	Intermediate Similarity	NPD7789	Approved
0.71	Intermediate Similarity	NPD7791	Approved
0.7097	Intermediate Similarity	NPD2008	Discontinued
0.7095	Intermediate Similarity	NPD5505	Discontinued
0.7089	Intermediate Similarity	NPD7777	Approved
0.7089	Intermediate Similarity	NPD7778	Approved
0.7089	Intermediate Similarity	NPD53	Approved
0.7079	Intermediate Similarity	NPD5065	Approved
0.7078	Intermediate Similarity	NPD6529	Discontinued
0.7075	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD8289	Discontinued
0.7059	Intermediate Similarity	NPD2411	Approved
0.7056	Intermediate Similarity	NPD4885	Approved
0.7053	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6987	Phase 1
0.7048	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8073	Approved
0.7033	Intermediate Similarity	NPD7234	Approved
0.7033	Intermediate Similarity	NPD7233	Approved
0.7031	Intermediate Similarity	NPD7731	Approved
0.7031	Intermediate Similarity	NPD7730	Approved
0.7027	Intermediate Similarity	NPD3795	Approved
0.7027	Intermediate Similarity	NPD3794	Approved
0.7024	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6595	Phase 3
0.7023	Intermediate Similarity	NPD484	Approved
0.7018	Intermediate Similarity	NPD7271	Approved
0.7015	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2144	Approved
0.7005	Intermediate Similarity	NPD3436	Approved
0.7005	Intermediate Similarity	NPD7564	Discontinued
0.7	Intermediate Similarity	NPD6281	Approved
0.6995	Remote Similarity	NPD2307	Discontinued
0.6991	Remote Similarity	NPD1996	Discontinued
0.6991	Remote Similarity	NPD5017	Discontinued
0.699	Remote Similarity	NPD3038	Discontinued
0.6987	Remote Similarity	NPD6276	Discontinued
0.6987	Remote Similarity	NPD7426	Phase 1
0.6986	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7878	Phase 2
0.6978	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5632	Approved
0.6977	Remote Similarity	NPD6249	Phase 2
0.6977	Remote Similarity	NPD6248	Phase 2
0.6976	Remote Similarity	NPD4076	Approved
0.6976	Remote Similarity	NPD4079	Approved
0.6971	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5075	Discontinued
0.697	Remote Similarity	NPD7824	Approved
0.697	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD2844	Phase 3
0.6963	Remote Similarity	NPD6664	Approved
0.6961	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4334	Discontinued
0.6947	Remote Similarity	NPD1722	Approved
0.6942	Remote Similarity	NPD5473	Discontinued
0.6941	Remote Similarity	NPD7010	Phase 3
0.6938	Remote Similarity	NPD5444	Phase 1
0.6937	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4376	Phase 3
0.6933	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4397	Phase 1
0.6929	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3506	Approved
0.6927	Remote Similarity	NPD5487	Phase 1
0.6927	Remote Similarity	NPD3505	Approved
0.6926	Remote Similarity	NPD7780	Approved
0.6926	Remote Similarity	NPD7781	Approved
0.6923	Remote Similarity	NPD4520	Approved
0.692	Remote Similarity	NPD5293	Phase 2
0.6913	Remote Similarity	NPD7603	Discontinued
0.6911	Remote Similarity	NPD6531	Approved
0.6911	Remote Similarity	NPD6530	Approved
0.6908	Remote Similarity	NPD3435	Discontinued
0.6901	Remote Similarity	NPD1038	Approved
0.69	Remote Similarity	NPD3323	Discontinued
0.6895	Remote Similarity	NPD8272	Phase 2
0.6895	Remote Similarity	NPD4795	Phase 2
0.6892	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8247	Approved
0.6885	Remote Similarity	NPD8246	Approved
0.6884	Remote Similarity	NPD6206	Phase 1
0.6881	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7558	Phase 2
0.6878	Remote Similarity	NPD4075	Phase 2
0.6872	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5198	Approved
0.6872	Remote Similarity	NPD3402	Phase 1
0.6872	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5199	Approved
0.6864	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD4547	Phase 3
0.6856	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6665	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data