NPASS Compound

Structure

NPC302111 OpenBabel07101718282D 33 37 0 0 1 0 0 0 0 0999 V2000 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 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 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 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 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 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 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 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 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7852 5.6132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 1 1 1 0 0 0 15 16 1 0 0 0 0 16 23 1 1 0 0 0 17 24 1 6 0 0 0 17 26 1 0 0 0 0 18 25 1 1 0 0 0 18 27 1 0 0 0 0 19 25 1 1 0 0 0 19 28 1 0 0 0 0 20 27 1 6 0 0 0 20 29 1 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 25 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 24 1 1 0 0 0 24 3 1 6 0 0 0 25 4 1 1 0 0 0 26 27 1 6 0 0 0 27 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.3
Volume:	480.234
LogP:	2.171
LogD:	2.378
LogS:	-3.858
# Rotatable Bonds:	5
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	5.717
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-6.123
MDCK Permeability:	6.3196016526489984e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.861
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	91.67296600341797%
Volume Distribution (VD):	0.483
Pgp-substrate:	6.630642890930176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.522
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.45
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.18
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	2.133
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.681
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.732
Carcinogencity:	0.619
Eye Corrosion:	0.013
Eye Irritation:	0.033
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC302111

Natural Product ID:	NPC302111
*Common Name:**	Norquadrangularic Acid A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PLBUBUFCNAFBIN-IQPYMKAHSA-N
Standard InCHI:	InChI=1S/C27H42O6/c1-15(5-8-21(30)31)16-9-10-24(3)17-6-7-18-25(4,22(32)33)19(28)13-20(29)27(18)14-26(17,27)12-11-23(16,24)2/h15-20,28-29H,5-14H2,1-4H3,(H,30,31)(H,32,33)/t15-,16-,17+,18+,19+,20+,23-,24+,25+,26+,27-/m1/s1
SMILES:	C[C@H](CCC(=O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](C[C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479490
PubChem CID:	10790237
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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]

☑ 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
ED50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	100.0	ug ml-1	PMID[545806]

☑ 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 NPC302111 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	393
0.1-0.2	3355
0.2-0.3	9501
0.3-0.4	13765
0.4-0.5	5946
0.5-0.6	5513
0.6-0.7	3213
0.7-0.8	869
0.8-0.85	92
0.85-0.9	42
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC56962
0.9639	High Similarity	NPC24705
0.925	High Similarity	NPC477851
0.9091	High Similarity	NPC288906
0.9091	High Similarity	NPC263135
0.9036	High Similarity	NPC50438
0.9	High Similarity	NPC224802
0.9	High Similarity	NPC324700
0.9	High Similarity	NPC34046
0.9	High Similarity	NPC80089
0.9	High Similarity	NPC171426
0.8889	High Similarity	NPC80891
0.8889	High Similarity	NPC201276
0.8889	High Similarity	NPC320144
0.881	High Similarity	NPC473336
0.881	High Similarity	NPC471044
0.881	High Similarity	NPC319909
0.8778	High Similarity	NPC234564
0.8765	High Similarity	NPC185465
0.875	High Similarity	NPC4209
0.8721	High Similarity	NPC263802
0.8706	High Similarity	NPC473350
0.8696	High Similarity	NPC41971
0.8696	High Similarity	NPC94906
0.8696	High Similarity	NPC37047
0.8696	High Similarity	NPC180733
0.8675	High Similarity	NPC12933
0.8667	High Similarity	NPC62407
0.8667	High Similarity	NPC287354
0.8652	High Similarity	NPC476189
0.8642	High Similarity	NPC207010
0.8642	High Similarity	NPC317913
0.8636	High Similarity	NPC77756
0.8625	High Similarity	NPC212733
0.8605	High Similarity	NPC472272
0.8605	High Similarity	NPC83242
0.8602	High Similarity	NPC71706
0.8587	High Similarity	NPC472028
0.8571	High Similarity	NPC121121
0.8539	High Similarity	NPC52756
0.8523	High Similarity	NPC61688
0.8511	High Similarity	NPC193934
0.8511	High Similarity	NPC271980
0.8511	High Similarity	NPC124544
0.85	High Similarity	NPC477930
0.85	High Similarity	NPC167702
0.85	High Similarity	NPC280026
0.8462	Intermediate Similarity	NPC266431
0.8452	Intermediate Similarity	NPC469745
0.8427	Intermediate Similarity	NPC476296
0.8421	Intermediate Similarity	NPC312900
0.8415	Intermediate Similarity	NPC298168
0.8415	Intermediate Similarity	NPC143133
0.8409	Intermediate Similarity	NPC146937
0.8409	Intermediate Similarity	NPC477614
0.8409	Intermediate Similarity	NPC226491
0.8404	Intermediate Similarity	NPC75941
0.8395	Intermediate Similarity	NPC273366
0.8395	Intermediate Similarity	NPC159789
0.8372	Intermediate Similarity	NPC237938
0.8372	Intermediate Similarity	NPC219535
0.8372	Intermediate Similarity	NPC477434
0.8353	Intermediate Similarity	NPC61107
0.8353	Intermediate Similarity	NPC268040
0.8353	Intermediate Similarity	NPC289486
0.8353	Intermediate Similarity	NPC30583
0.8333	Intermediate Similarity	NPC201763
0.8295	Intermediate Similarity	NPC252714
0.8293	Intermediate Similarity	NPC477933
0.8293	Intermediate Similarity	NPC472487
0.8293	Intermediate Similarity	NPC472486
0.8293	Intermediate Similarity	NPC474020
0.8293	Intermediate Similarity	NPC477932
0.8235	Intermediate Similarity	NPC476071
0.8193	Intermediate Similarity	NPC221420
0.8193	Intermediate Similarity	NPC477918
0.8193	Intermediate Similarity	NPC475031
0.8172	Intermediate Similarity	NPC116683
0.8171	Intermediate Similarity	NPC21220
0.8171	Intermediate Similarity	NPC125767
0.8171	Intermediate Similarity	NPC477934
0.8163	Intermediate Similarity	NPC263729
0.8148	Intermediate Similarity	NPC232112
0.8132	Intermediate Similarity	NPC198242
0.8132	Intermediate Similarity	NPC211403
0.8125	Intermediate Similarity	NPC477850
0.8118	Intermediate Similarity	NPC261616
0.8111	Intermediate Similarity	NPC200580
0.8111	Intermediate Similarity	NPC57954
0.8111	Intermediate Similarity	NPC213832
0.8111	Intermediate Similarity	NPC67653
0.8111	Intermediate Similarity	NPC471459
0.8095	Intermediate Similarity	NPC329117
0.809	Intermediate Similarity	NPC202937
0.8085	Intermediate Similarity	NPC469810
0.8081	Intermediate Similarity	NPC163216
0.8072	Intermediate Similarity	NPC475742
0.8072	Intermediate Similarity	NPC5767
0.8068	Intermediate Similarity	NPC131350
0.8068	Intermediate Similarity	NPC477205
0.8065	Intermediate Similarity	NPC17336
0.8065	Intermediate Similarity	NPC470031
0.8046	Intermediate Similarity	NPC327451
0.8043	Intermediate Similarity	NPC244356
0.8043	Intermediate Similarity	NPC224060
0.8025	Intermediate Similarity	NPC156277
0.8025	Intermediate Similarity	NPC151018
0.8025	Intermediate Similarity	NPC473267
0.8025	Intermediate Similarity	NPC320549
0.8025	Intermediate Similarity	NPC58057
0.8023	Intermediate Similarity	NPC58631
0.8022	Intermediate Similarity	NPC88337
0.8022	Intermediate Similarity	NPC475211
0.8021	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC476734
0.8	Intermediate Similarity	NPC252032
0.8	Intermediate Similarity	NPC471900
0.8	Intermediate Similarity	NPC52951
0.8	Intermediate Similarity	NPC3032
0.8	Intermediate Similarity	NPC285298
0.8	Intermediate Similarity	NPC473319
0.8	Intermediate Similarity	NPC469941
0.8	Intermediate Similarity	NPC257082
0.8	Intermediate Similarity	NPC131104
0.8	Intermediate Similarity	NPC319671
0.7979	Intermediate Similarity	NPC329910
0.7979	Intermediate Similarity	NPC193785
0.7978	Intermediate Similarity	NPC476726
0.7978	Intermediate Similarity	NPC80700
0.7978	Intermediate Similarity	NPC476727
0.7976	Intermediate Similarity	NPC264602
0.7976	Intermediate Similarity	NPC471151
0.7957	Intermediate Similarity	NPC470385
0.7957	Intermediate Similarity	NPC470386
0.7955	Intermediate Similarity	NPC473299
0.7952	Intermediate Similarity	NPC174964
0.7952	Intermediate Similarity	NPC195155
0.7952	Intermediate Similarity	NPC472311
0.7952	Intermediate Similarity	NPC97534
0.7938	Intermediate Similarity	NPC88203
0.7938	Intermediate Similarity	NPC76866
0.7938	Intermediate Similarity	NPC275990
0.7938	Intermediate Similarity	NPC246736
0.7938	Intermediate Similarity	NPC214946
0.7938	Intermediate Similarity	NPC286519
0.7938	Intermediate Similarity	NPC304832
0.7938	Intermediate Similarity	NPC148628
0.7931	Intermediate Similarity	NPC202688
0.7931	Intermediate Similarity	NPC154043
0.7931	Intermediate Similarity	NPC60018
0.7931	Intermediate Similarity	NPC477935
0.7931	Intermediate Similarity	NPC317066
0.7931	Intermediate Similarity	NPC13494
0.7912	Intermediate Similarity	NPC477440
0.7912	Intermediate Similarity	NPC477443
0.7907	Intermediate Similarity	NPC470609
0.7901	Intermediate Similarity	NPC477929
0.7895	Intermediate Similarity	NPC472273
0.7895	Intermediate Similarity	NPC170978
0.7895	Intermediate Similarity	NPC253586
0.7889	Intermediate Similarity	NPC264005
0.7889	Intermediate Similarity	NPC269360
0.7889	Intermediate Similarity	NPC239938
0.7872	Intermediate Similarity	NPC82633
0.7872	Intermediate Similarity	NPC470232
0.7872	Intermediate Similarity	NPC470229
0.7857	Intermediate Similarity	NPC471046
0.7857	Intermediate Similarity	NPC470310
0.7849	Intermediate Similarity	NPC471902
0.7849	Intermediate Similarity	NPC473690
0.7849	Intermediate Similarity	NPC287118
0.7849	Intermediate Similarity	NPC477855
0.7843	Intermediate Similarity	NPC270586
0.7841	Intermediate Similarity	NPC15091
0.7835	Intermediate Similarity	NPC52899
0.7835	Intermediate Similarity	NPC163963
0.7835	Intermediate Similarity	NPC289148
0.7831	Intermediate Similarity	NPC133922
0.7831	Intermediate Similarity	NPC254340
0.7826	Intermediate Similarity	NPC477442
0.7826	Intermediate Similarity	NPC169933
0.7826	Intermediate Similarity	NPC477433
0.7826	Intermediate Similarity	NPC477444
0.7816	Intermediate Similarity	NPC254123
0.7812	Intermediate Similarity	NPC98837
0.7812	Intermediate Similarity	NPC474793
0.7812	Intermediate Similarity	NPC38296
0.7812	Intermediate Similarity	NPC20479
0.7812	Intermediate Similarity	NPC471038
0.7812	Intermediate Similarity	NPC162459
0.7812	Intermediate Similarity	NPC476294
0.7812	Intermediate Similarity	NPC28864
0.7812	Intermediate Similarity	NPC38471
0.7805	Intermediate Similarity	NPC89310
0.7805	Intermediate Similarity	NPC469940
0.7802	Intermediate Similarity	NPC476435
0.7802	Intermediate Similarity	NPC476379
0.7791	Intermediate Similarity	NPC472310
0.7791	Intermediate Similarity	NPC220379
0.7789	Intermediate Similarity	NPC470387

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 NPC302111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	420
0.1-0.2	3561
0.2-0.3	3460
0.3-0.4	1029
0.4-0.5	291
0.5-0.6	239
0.6-0.7	121
0.7-0.8	21
0.8-0.85	2
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD6697	Approved
0.9	High Similarity	NPD6115	Approved
0.9	High Similarity	NPD6114	Approved
0.9	High Similarity	NPD6118	Approved
0.875	High Similarity	NPD6117	Approved
0.8642	High Similarity	NPD6116	Phase 1
0.85	High Similarity	NPD6113	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD3703	Phase 2
0.8025	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6081	Approved
0.747	Intermediate Similarity	NPD4245	Approved
0.747	Intermediate Similarity	NPD4789	Approved
0.747	Intermediate Similarity	NPD4244	Approved
0.7439	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5360	Phase 3
0.7407	Intermediate Similarity	NPD4224	Phase 2
0.7349	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3698	Phase 2
0.7326	Intermediate Similarity	NPD3702	Approved
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8418	Phase 2
0.7188	Intermediate Similarity	NPD8034	Phase 2
0.7188	Intermediate Similarity	NPD8035	Phase 2
0.7176	Intermediate Similarity	NPD5777	Approved
0.7129	Intermediate Similarity	NPD1700	Approved
0.7079	Intermediate Similarity	NPD3671	Phase 1
0.6979	Remote Similarity	NPD5328	Approved
0.6977	Remote Similarity	NPD4758	Discontinued
0.6923	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5364	Discontinued
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7128	Approved
0.6857	Remote Similarity	NPD6675	Approved
0.6857	Remote Similarity	NPD6402	Approved
0.6857	Remote Similarity	NPD5739	Approved
0.6837	Remote Similarity	NPD6079	Approved
0.6765	Remote Similarity	NPD7638	Approved
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD7320	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD4786	Approved
0.6606	Remote Similarity	NPD4634	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.66	Remote Similarity	NPD6399	Phase 3
0.6571	Remote Similarity	NPD7632	Discontinued
0.6569	Remote Similarity	NPD5222	Approved
0.6569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4697	Phase 3
0.6569	Remote Similarity	NPD5221	Approved
0.6559	Remote Similarity	NPD6928	Phase 2
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6538	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD5285	Approved
0.6538	Remote Similarity	NPD4696	Approved
0.6538	Remote Similarity	NPD4700	Approved
0.6526	Remote Similarity	NPD4788	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD7319	Approved
0.6495	Remote Similarity	NPD3618	Phase 1
0.6486	Remote Similarity	NPD6882	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6463	Remote Similarity	NPD3198	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6429	Remote Similarity	NPD8298	Phase 2
0.6429	Remote Similarity	NPD4632	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.6417	Remote Similarity	NPD7736	Approved
0.6415	Remote Similarity	NPD5226	Approved
0.6415	Remote Similarity	NPD4633	Approved
0.6415	Remote Similarity	NPD5224	Approved
0.6415	Remote Similarity	NPD5225	Approved
0.6415	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7115	Discovery
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6008	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6383	Remote Similarity	NPD7525	Registered
0.6379	Remote Similarity	NPD6059	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7604	Phase 2
0.6355	Remote Similarity	NPD5174	Approved
0.6355	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6344	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD4238	Approved
0.6337	Remote Similarity	NPD7637	Suspended
0.6337	Remote Similarity	NPD6411	Approved
0.6333	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD7078	Approved
0.6321	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD6940	Discontinued
0.6296	Remote Similarity	NPD5141	Approved
0.6283	Remote Similarity	NPD8133	Approved
0.6275	Remote Similarity	NPD4202	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4767	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD4754	Approved
0.619	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD6016	Approved
0.6174	Remote Similarity	NPD6274	Approved
0.6174	Remote Similarity	NPD6868	Approved
0.6163	Remote Similarity	NPD7909	Approved
0.6162	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7100	Approved
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD5988	Approved
0.6126	Remote Similarity	NPD4729	Approved
0.6126	Remote Similarity	NPD5128	Approved
0.6126	Remote Similarity	NPD4730	Approved
0.6122	Remote Similarity	NPD3665	Phase 1
0.6122	Remote Similarity	NPD3133	Approved
0.6122	Remote Similarity	NPD3666	Approved
0.6117	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD8171	Discontinued
0.6117	Remote Similarity	NPD5778	Approved
0.6083	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD6700	Approved
0.6078	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6335	Approved
0.605	Remote Similarity	NPD6908	Approved
0.605	Remote Similarity	NPD5983	Phase 2
0.605	Remote Similarity	NPD6909	Approved
0.604	Remote Similarity	NPD5737	Approved
0.604	Remote Similarity	NPD6672	Approved
0.604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6702	Approved
0.6019	Remote Similarity	NPD6703	Approved
0.6018	Remote Similarity	NPD5250	Approved
0.6018	Remote Similarity	NPD5249	Phase 3
0.6018	Remote Similarity	NPD5248	Approved
0.6018	Remote Similarity	NPD5251	Approved
0.6018	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5983	Remote Similarity	NPD6317	Approved
0.5982	Remote Similarity	NPD5168	Approved
0.5981	Remote Similarity	NPD5696	Approved
0.5965	Remote Similarity	NPD5216	Approved
0.5965	Remote Similarity	NPD5215	Approved
0.5965	Remote Similarity	NPD5217	Approved
0.596	Remote Similarity	NPD3668	Phase 3
0.5946	Remote Similarity	NPD6920	Discontinued
0.5932	Remote Similarity	NPD6314	Approved
0.5932	Remote Similarity	NPD6313	Approved
0.5905	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7900	Approved
0.5893	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6412	Phase 2
0.5889	Remote Similarity	NPD229	Approved
0.5887	Remote Similarity	NPD6033	Approved
0.5882	Remote Similarity	NPD6903	Approved
0.5877	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5169	Approved

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