NPASS Compound

Structure

NPC474996 OpenBabel07101719512D 34 40 0 0 1 0 0 0 0 0999 V2000 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2794 -2.6601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5884 -1.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7375 -2.1045 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 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 4.9885 -2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6284 -1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2757 -1.5454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 4.3194 -1.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9666 -2.4965 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 6.6102 -1.9170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4302 -1.0699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 30 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 17 30 1 0 0 0 0 17 31 1 0 0 0 0 18 13 1 6 0 0 0 18 21 1 0 0 0 0 19 13 1 1 0 0 0 19 27 1 0 0 0 0 20 14 1 6 0 0 0 20 34 1 0 0 0 0 21 28 1 1 0 0 0 22 25 1 0 0 0 0 22 32 2 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 27 34 1 0 0 0 0 28 29 1 1 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.36
Volume:	508.571
LogP:	6.68
LogD:	5.007
LogS:	-5.06
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	6.709
Fsp3:	0.968
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.222
MDCK Permeability:	1.1802701919805259e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.342
Plasma Protein Binding (PPB):	93.20791625976562%
Volume Distribution (VD):	1.234
Pgp-substrate:	2.8972442150115967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	11.448
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.407
Human Hepatotoxicity (H-HT):	0.571
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.923
Carcinogencity:	0.869
Eye Corrosion:	0.016
Eye Irritation:	0.035
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC474996

Natural Product ID:	NPC474996
*Common Name:**	Monocarpinine
IUPAC Name:	n.a.
Synonyms:	Monocarpinine
Standard InCHIKey:	LEZYGKKZDLFXBV-IWMNKMOUSA-N
Standard InCHI:	InChI=1S/C31H48O3/c1-26(2)23-7-8-24-29(6)10-9-21(18-13-19-15-20(14-18)34-27(19,3)4)28(29,5)11-12-30(24)17-31(23,30)16-22(32)25(26)33/h18-21,23-25,33H,7-17H2,1-6H3/t18-,19-,20-,21+,23-,24-,25-,28+,29-,30-,31+/m0/s1
SMILES:	CC1(C2CCC3C4(CCC(C4(CCC35C2(C5)CC(=O)C1O)C)C6CC7CC(C6)OC7(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491459
PubChem CID:	44585959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO18362	Monocarpia marginalis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18462006]
NPO18362	Monocarpia marginalis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[572958]

☑ 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 NPC474996 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	392
0.1-0.2	3763
0.2-0.3	14690
0.3-0.4	10125
0.4-0.5	5448
0.5-0.6	5241
0.6-0.7	2510
0.7-0.8	483
0.8-0.85	37
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8861	High Similarity	NPC475031
0.8861	High Similarity	NPC23884
0.8846	High Similarity	NPC195155
0.8846	High Similarity	NPC273366
0.8846	High Similarity	NPC174964
0.8846	High Similarity	NPC97534
0.8734	High Similarity	NPC5767
0.8734	High Similarity	NPC475742
0.8718	High Similarity	NPC254340
0.8659	High Similarity	NPC58631
0.8625	High Similarity	NPC221420
0.859	High Similarity	NPC232112
0.8571	High Similarity	NPC105895
0.8554	High Similarity	NPC289486
0.8554	High Similarity	NPC61107
0.8462	Intermediate Similarity	NPC156277
0.8462	Intermediate Similarity	NPC320549
0.8462	Intermediate Similarity	NPC58057
0.8462	Intermediate Similarity	NPC151018
0.8434	Intermediate Similarity	NPC50658
0.8395	Intermediate Similarity	NPC143133
0.8395	Intermediate Similarity	NPC298168
0.8375	Intermediate Similarity	NPC267753
0.8372	Intermediate Similarity	NPC80700
0.8313	Intermediate Similarity	NPC261616
0.8295	Intermediate Similarity	NPC122116
0.8272	Intermediate Similarity	NPC472486
0.8272	Intermediate Similarity	NPC472487
0.825	Intermediate Similarity	NPC130011
0.8235	Intermediate Similarity	NPC472744
0.8235	Intermediate Similarity	NPC327451
0.8228	Intermediate Similarity	NPC473279
0.8228	Intermediate Similarity	NPC89310
0.8214	Intermediate Similarity	NPC48756
0.8214	Intermediate Similarity	NPC280781
0.8214	Intermediate Similarity	NPC469745
0.8214	Intermediate Similarity	NPC12933
0.8205	Intermediate Similarity	NPC6120
0.8205	Intermediate Similarity	NPC213178
0.8205	Intermediate Similarity	NPC131892
0.8205	Intermediate Similarity	NPC327728
0.8193	Intermediate Similarity	NPC31302
0.8193	Intermediate Similarity	NPC245029
0.8171	Intermediate Similarity	NPC264602
0.8161	Intermediate Similarity	NPC92139
0.8161	Intermediate Similarity	NPC474448
0.8148	Intermediate Similarity	NPC72444
0.8148	Intermediate Similarity	NPC212733
0.8148	Intermediate Similarity	NPC125767
0.8148	Intermediate Similarity	NPC21220
0.814	Intermediate Similarity	NPC319909
0.814	Intermediate Similarity	NPC25037
0.814	Intermediate Similarity	NPC474233
0.814	Intermediate Similarity	NPC34984
0.8125	Intermediate Similarity	NPC282905
0.8125	Intermediate Similarity	NPC477229
0.8125	Intermediate Similarity	NPC474123
0.8125	Intermediate Similarity	NPC81759
0.8125	Intermediate Similarity	NPC68426
0.8118	Intermediate Similarity	NPC268040
0.8118	Intermediate Similarity	NPC328007
0.8118	Intermediate Similarity	NPC30583
0.809	Intermediate Similarity	NPC61688
0.8077	Intermediate Similarity	NPC473225
0.8068	Intermediate Similarity	NPC202937
0.8049	Intermediate Similarity	NPC4209
0.8043	Intermediate Similarity	NPC470031
0.8043	Intermediate Similarity	NPC305808
0.8025	Intermediate Similarity	NPC168511
0.8025	Intermediate Similarity	NPC167702
0.8025	Intermediate Similarity	NPC159325
0.8025	Intermediate Similarity	NPC280026
0.8023	Intermediate Similarity	NPC472743
0.8023	Intermediate Similarity	NPC217559
0.8023	Intermediate Similarity	NPC292458
0.8023	Intermediate Similarity	NPC475726
0.8023	Intermediate Similarity	NPC268578
0.8022	Intermediate Similarity	NPC472232
0.8022	Intermediate Similarity	NPC472231
0.8	Intermediate Similarity	NPC195530
0.8	Intermediate Similarity	NPC473267
0.8	Intermediate Similarity	NPC77311
0.7976	Intermediate Similarity	NPC320144
0.7976	Intermediate Similarity	NPC80891
0.7976	Intermediate Similarity	NPC201276
0.7957	Intermediate Similarity	NPC476728
0.7955	Intermediate Similarity	NPC476727
0.7955	Intermediate Similarity	NPC476726
0.7952	Intermediate Similarity	NPC317913
0.7952	Intermediate Similarity	NPC207010
0.7949	Intermediate Similarity	NPC48079
0.7935	Intermediate Similarity	NPC206878
0.7931	Intermediate Similarity	NPC473336
0.7931	Intermediate Similarity	NPC474482
0.7931	Intermediate Similarity	NPC471044
0.7931	Intermediate Similarity	NPC475745
0.7927	Intermediate Similarity	NPC159789
0.7901	Intermediate Similarity	NPC310766
0.7882	Intermediate Similarity	NPC477851
0.7875	Intermediate Similarity	NPC282454
0.7857	Intermediate Similarity	NPC185465
0.7857	Intermediate Similarity	NPC80089
0.7857	Intermediate Similarity	NPC324700
0.7857	Intermediate Similarity	NPC26029
0.7857	Intermediate Similarity	NPC224802
0.7857	Intermediate Similarity	NPC34046
0.7857	Intermediate Similarity	NPC171426
0.7848	Intermediate Similarity	NPC472741
0.7841	Intermediate Similarity	NPC76518
0.7841	Intermediate Similarity	NPC62572
0.7841	Intermediate Similarity	NPC292553
0.7831	Intermediate Similarity	NPC108840
0.7826	Intermediate Similarity	NPC472148
0.7826	Intermediate Similarity	NPC472147
0.7821	Intermediate Similarity	NPC142712
0.7805	Intermediate Similarity	NPC472854
0.7805	Intermediate Similarity	NPC477508
0.7805	Intermediate Similarity	NPC133922
0.7802	Intermediate Similarity	NPC77756
0.7778	Intermediate Similarity	NPC157422
0.7778	Intermediate Similarity	NPC90676
0.7778	Intermediate Similarity	NPC100586
0.7778	Intermediate Similarity	NPC109457
0.7765	Intermediate Similarity	NPC220379
0.7753	Intermediate Similarity	NPC472738
0.7753	Intermediate Similarity	NPC12774
0.7753	Intermediate Similarity	NPC472745
0.775	Intermediate Similarity	NPC324607
0.775	Intermediate Similarity	NPC321732
0.775	Intermediate Similarity	NPC129829
0.775	Intermediate Similarity	NPC254037
0.775	Intermediate Similarity	NPC299948
0.775	Intermediate Similarity	NPC241085
0.775	Intermediate Similarity	NPC470830
0.7738	Intermediate Similarity	NPC474404
0.7727	Intermediate Similarity	NPC264665
0.7727	Intermediate Similarity	NPC74595
0.7727	Intermediate Similarity	NPC50438
0.7727	Intermediate Similarity	NPC473299
0.7722	Intermediate Similarity	NPC475884
0.7722	Intermediate Similarity	NPC473230
0.7717	Intermediate Similarity	NPC52756
0.7711	Intermediate Similarity	NPC270306
0.7711	Intermediate Similarity	NPC91387
0.7711	Intermediate Similarity	NPC231680
0.7701	Intermediate Similarity	NPC13494
0.7701	Intermediate Similarity	NPC317066
0.7692	Intermediate Similarity	NPC474380
0.7692	Intermediate Similarity	NPC41577
0.7692	Intermediate Similarity	NPC473276
0.7683	Intermediate Similarity	NPC472341
0.7683	Intermediate Similarity	NPC473238
0.7674	Intermediate Similarity	NPC470609
0.7667	Intermediate Similarity	NPC252714
0.7667	Intermediate Similarity	NPC33768
0.7667	Intermediate Similarity	NPC57469
0.7667	Intermediate Similarity	NPC4643
0.7654	Intermediate Similarity	NPC477850
0.7654	Intermediate Similarity	NPC192192
0.7654	Intermediate Similarity	NPC477929
0.7654	Intermediate Similarity	NPC108131
0.7654	Intermediate Similarity	NPC231945
0.7647	Intermediate Similarity	NPC243594
0.7647	Intermediate Similarity	NPC31031
0.7647	Intermediate Similarity	NPC478128
0.764	Intermediate Similarity	NPC294438
0.764	Intermediate Similarity	NPC477445
0.764	Intermediate Similarity	NPC264317
0.7634	Intermediate Similarity	NPC161035
0.7634	Intermediate Similarity	NPC12722
0.7625	Intermediate Similarity	NPC2568
0.7625	Intermediate Similarity	NPC103647
0.7625	Intermediate Similarity	NPC180777
0.7625	Intermediate Similarity	NPC260319
0.7625	Intermediate Similarity	NPC474954
0.7614	Intermediate Similarity	NPC269684
0.7609	Intermediate Similarity	NPC475056
0.7609	Intermediate Similarity	NPC46758
0.7586	Intermediate Similarity	NPC271572
0.7586	Intermediate Similarity	NPC73515
0.7586	Intermediate Similarity	NPC474870
0.7586	Intermediate Similarity	NPC328264
0.7582	Intermediate Similarity	NPC474719
0.7582	Intermediate Similarity	NPC4309
0.7582	Intermediate Similarity	NPC477614
0.7582	Intermediate Similarity	NPC226491
0.7582	Intermediate Similarity	NPC472739
0.7576	Intermediate Similarity	NPC327093
0.7564	Intermediate Similarity	NPC69149
0.7561	Intermediate Similarity	NPC247195
0.7561	Intermediate Similarity	NPC469940
0.7561	Intermediate Similarity	NPC197701
0.7561	Intermediate Similarity	NPC127094
0.7558	Intermediate Similarity	NPC73013
0.7558	Intermediate Similarity	NPC275243
0.7558	Intermediate Similarity	NPC201459
0.7558	Intermediate Similarity	NPC52951
0.7556	Intermediate Similarity	NPC269396
0.7556	Intermediate Similarity	NPC302111
0.7556	Intermediate Similarity	NPC98236

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 NPC474996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	3851
0.2-0.3	3482
0.3-0.4	844
0.4-0.5	211
0.5-0.6	209
0.6-0.7	102
0.7-0.8	26
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4789	Approved
0.8205	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5360	Phase 3
0.8077	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6117	Approved
0.8025	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6116	Phase 1
0.7927	Intermediate Similarity	NPD3703	Phase 2
0.7875	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD4245	Approved
0.7857	Intermediate Similarity	NPD6114	Approved
0.7857	Intermediate Similarity	NPD6697	Approved
0.7857	Intermediate Similarity	NPD6118	Approved
0.7857	Intermediate Similarity	NPD6115	Approved
0.775	Intermediate Similarity	NPD3698	Phase 2
0.7692	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4758	Discontinued
0.7442	Intermediate Similarity	NPD3671	Phase 1
0.7349	Intermediate Similarity	NPD5777	Approved
0.734	Intermediate Similarity	NPD8035	Phase 2
0.734	Intermediate Similarity	NPD8034	Phase 2
0.7317	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3702	Approved
0.7241	Intermediate Similarity	NPD5364	Discontinued
0.716	Intermediate Similarity	NPD4224	Phase 2
0.7143	Intermediate Similarity	NPD6081	Approved
0.7079	Intermediate Similarity	NPD6928	Phase 2
0.7033	Intermediate Similarity	NPD4788	Approved
0.7024	Intermediate Similarity	NPD4787	Phase 1
0.6957	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD5328	Approved
0.6893	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7320	Approved
0.6827	Remote Similarity	NPD7128	Approved
0.6827	Remote Similarity	NPD6675	Approved
0.6827	Remote Similarity	NPD5739	Approved
0.6827	Remote Similarity	NPD6402	Approved
0.6809	Remote Similarity	NPD3618	Phase 1
0.6804	Remote Similarity	NPD6079	Approved
0.68	Remote Similarity	NPD4755	Approved
0.6739	Remote Similarity	NPD3667	Approved
0.6735	Remote Similarity	NPD4202	Approved
0.67	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD5221	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6698	Remote Similarity	NPD6899	Approved
0.6698	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD6920	Discontinued
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6634	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD5173	Approved
0.6634	Remote Similarity	NPD6083	Phase 2
0.6633	Remote Similarity	NPD7515	Phase 2
0.6604	Remote Similarity	NPD5701	Approved
0.6604	Remote Similarity	NPD5697	Approved
0.6602	Remote Similarity	NPD5223	Approved
0.66	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4753	Phase 2
0.6574	Remote Similarity	NPD7102	Approved
0.6574	Remote Similarity	NPD7290	Approved
0.6574	Remote Similarity	NPD6883	Approved
0.6566	Remote Similarity	NPD6399	Phase 3
0.6542	Remote Similarity	NPD6011	Approved
0.6538	Remote Similarity	NPD5226	Approved
0.6538	Remote Similarity	NPD5225	Approved
0.6538	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD5211	Phase 2
0.6538	Remote Similarity	NPD5224	Approved
0.6526	Remote Similarity	NPD5329	Approved
0.6522	Remote Similarity	NPD7525	Registered
0.6514	Remote Similarity	NPD6649	Approved
0.6514	Remote Similarity	NPD6869	Approved
0.6514	Remote Similarity	NPD6617	Approved
0.6514	Remote Similarity	NPD6847	Approved
0.6514	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD8130	Phase 1
0.6484	Remote Similarity	NPD3617	Approved
0.6481	Remote Similarity	NPD6012	Approved
0.6481	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD6013	Approved
0.6476	Remote Similarity	NPD4754	Approved
0.6476	Remote Similarity	NPD5175	Approved
0.6476	Remote Similarity	NPD5174	Approved
0.6471	Remote Similarity	NPD7902	Approved
0.6458	Remote Similarity	NPD5279	Phase 3
0.6455	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6442	Remote Similarity	NPD1700	Approved
0.6421	Remote Similarity	NPD4197	Approved
0.6421	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD5141	Approved
0.6389	Remote Similarity	NPD6415	Discontinued
0.6355	Remote Similarity	NPD4768	Approved
0.6355	Remote Similarity	NPD4767	Approved
0.6348	Remote Similarity	NPD6059	Approved
0.6348	Remote Similarity	NPD6054	Approved
0.6346	Remote Similarity	NPD8418	Phase 2
0.6337	Remote Similarity	NPD6001	Approved
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6672	Approved
0.6327	Remote Similarity	NPD5737	Approved
0.6289	Remote Similarity	NPD6098	Approved
0.6275	Remote Similarity	NPD4629	Approved
0.6275	Remote Similarity	NPD5695	Phase 3
0.6275	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD7736	Approved
0.6239	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6237	Remote Similarity	NPD7645	Phase 2
0.6228	Remote Similarity	NPD7115	Discovery
0.6211	Remote Similarity	NPD4221	Approved
0.6211	Remote Similarity	NPD4223	Phase 3
0.6204	Remote Similarity	NPD6008	Approved
0.619	Remote Similarity	NPD7640	Approved
0.619	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7604	Phase 2
0.6176	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7900	Approved
0.6174	Remote Similarity	NPD6335	Approved
0.6162	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD6016	Approved
0.6154	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6015	Approved
0.614	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD6868	Approved
0.6134	Remote Similarity	NPD7492	Approved
0.6126	Remote Similarity	NPD5135	Approved
0.6126	Remote Similarity	NPD5169	Approved
0.6126	Remote Similarity	NPD5251	Approved
0.6126	Remote Similarity	NPD5250	Approved
0.6126	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4634	Approved
0.6126	Remote Similarity	NPD5249	Phase 3
0.6126	Remote Similarity	NPD5248	Approved
0.6126	Remote Similarity	NPD5247	Approved
0.6122	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5690	Phase 2
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD4694	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD5280	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6121	Remote Similarity	NPD7101	Approved
0.6121	Remote Similarity	NPD7100	Approved
0.6106	Remote Similarity	NPD4632	Approved
0.6105	Remote Similarity	NPD4139	Approved
0.6105	Remote Similarity	NPD4692	Approved
0.6102	Remote Similarity	NPD5988	Approved
0.61	Remote Similarity	NPD6080	Approved
0.61	Remote Similarity	NPD6673	Approved
0.61	Remote Similarity	NPD6904	Approved
0.6091	Remote Similarity	NPD5168	Approved
0.6091	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6317	Approved
0.6083	Remote Similarity	NPD6616	Approved
0.6082	Remote Similarity	NPD3668	Phase 3
0.6078	Remote Similarity	NPD5133	Approved
0.6075	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD5215	Approved
0.6071	Remote Similarity	NPD5217	Approved
0.6071	Remote Similarity	NPD5127	Approved
0.6071	Remote Similarity	NPD5216	Approved
0.6034	Remote Similarity	NPD6313	Approved
0.6034	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD8293	Discontinued
0.6033	Remote Similarity	NPD7078	Approved
0.6024	Remote Similarity	NPD3198	Approved
0.6017	Remote Similarity	NPD6909	Approved
0.6017	Remote Similarity	NPD6908	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5978	Remote Similarity	NPD6942	Approved
0.5978	Remote Similarity	NPD7339	Approved
0.5965	Remote Similarity	NPD8133	Approved
0.5962	Remote Similarity	NPD7991	Discontinued
0.596	Remote Similarity	NPD4690	Approved
0.596	Remote Similarity	NPD4688	Approved
0.596	Remote Similarity	NPD4689	Approved
0.596	Remote Similarity	NPD4693	Phase 3

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