NPASS Compound

Structure

CID212733 OpenBabel06191716002D 26 29 0 0 1 0 0 0 0 0999 V2000 2.9948 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0281 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4440 0.3998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7565 -0.1846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7565 -1.7487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8372 -1.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 0.9667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8372 -0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3486 0.9667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0552 -2.6681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8372 -0.4833 0.0000 C 0 0 1 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 4.1858 1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0008 -2.8691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4084 -3.3864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 4 22 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 22 1 6 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 21 1 1 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 1 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 21 3 1 1 0 0 0 22 23 1 1 0 0 0 23 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.28
Volume:	395.873
LogP:	4.223
LogD:	4.146
LogS:	-3.893
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	4.281
Fsp3:	0.957
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:	-5.339
MDCK Permeability:	4.584984344546683e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	94.69849395751953%
Volume Distribution (VD):	0.836
Pgp-substrate:	4.218103885650635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.652
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.658
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.513
Carcinogencity:	0.01
Eye Corrosion:	0.389
Eye Irritation:	0.853
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC212733

Natural Product ID:	NPC212733
*Common Name:**	3Beta-Hydroxyetio-17Beta-Dammaranic Acid
IUPAC Name:	(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
Synonyms:
Standard InCHIKey:	PTSOMORPIOAPGG-CSNGNCMSSA-N
Standard InCHI:	InChI=1S/C23H38O3/c1-20(2)16-9-13-23(5)17(21(16,3)11-10-18(20)24)7-6-15-14(19(25)26)8-12-22(15,23)4/h14-18,24H,6-13H2,1-5H3,(H,25,26)/t14-,15+,16-,17+,18-,21-,22+,23+/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@H](CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313420
PubChem CID:	71716739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

*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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	13100.0	nM	PMID[533182]

☑ 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 NPC212733 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	308
0.1-0.2	2918
0.2-0.3	13225
0.3-0.4	10917
0.4-0.5	5718
0.5-0.6	4970
0.6-0.7	3263
0.7-0.8	1125
0.8-0.85	158
0.85-0.9	51
0.9-0.95	32
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC4209
0.9855	High Similarity	NPC167702
0.9855	High Similarity	NPC280026
0.9718	High Similarity	NPC143133
0.9718	High Similarity	NPC207010
0.9718	High Similarity	NPC317913
0.9718	High Similarity	NPC298168
0.9583	High Similarity	NPC224802
0.9583	High Similarity	NPC324700
0.9583	High Similarity	NPC80089
0.9583	High Similarity	NPC34046
0.9583	High Similarity	NPC171426
0.9452	High Similarity	NPC80891
0.9452	High Similarity	NPC201276
0.9452	High Similarity	NPC320144
0.9429	High Similarity	NPC232112
0.9315	High Similarity	NPC185465
0.9286	High Similarity	NPC151018
0.9286	High Similarity	NPC58057
0.9286	High Similarity	NPC156277
0.9286	High Similarity	NPC320549
0.9275	High Similarity	NPC469941
0.9275	High Similarity	NPC252032
0.9275	High Similarity	NPC476734
0.9275	High Similarity	NPC319671
0.92	High Similarity	NPC12933
0.92	High Similarity	NPC58631
0.9167	High Similarity	NPC97534
0.9167	High Similarity	NPC273366
0.9167	High Similarity	NPC174964
0.9167	High Similarity	NPC195155
0.9143	High Similarity	NPC477929
0.9079	High Similarity	NPC289486
0.9079	High Similarity	NPC61107
0.9079	High Similarity	NPC30583
0.9079	High Similarity	NPC121121
0.9067	High Similarity	NPC477851
0.9067	High Similarity	NPC261616
0.9054	High Similarity	NPC329117
0.9041	High Similarity	NPC475742
0.9041	High Similarity	NPC5767
0.9041	High Similarity	NPC472487
0.9041	High Similarity	NPC472486
0.9028	High Similarity	NPC254340
0.9014	High Similarity	NPC89310
0.9	High Similarity	NPC6120
0.9	High Similarity	NPC213178
0.9	High Similarity	NPC196197
0.9	High Similarity	NPC327728
0.9	High Similarity	NPC131892
0.8919	High Similarity	NPC23884
0.8919	High Similarity	NPC221420
0.8919	High Similarity	NPC475031
0.8904	High Similarity	NPC21220
0.8904	High Similarity	NPC125767
0.8873	High Similarity	NPC477850
0.8846	High Similarity	NPC473336
0.8846	High Similarity	NPC471044
0.8841	High Similarity	NPC42060
0.8767	High Similarity	NPC477930
0.875	High Similarity	NPC469940
0.8734	High Similarity	NPC264317
0.8734	High Similarity	NPC294438
0.8732	High Similarity	NPC64466
0.8667	High Similarity	NPC477919
0.8667	High Similarity	NPC180199
0.8649	High Similarity	NPC472311
0.8649	High Similarity	NPC159789
0.863	High Similarity	NPC310766
0.8625	High Similarity	NPC472272
0.8625	High Similarity	NPC12774
0.8625	High Similarity	NPC2783
0.8625	High Similarity	NPC302111
0.8611	High Similarity	NPC108131
0.8608	High Similarity	NPC319909
0.8571	High Similarity	NPC477931
0.8571	High Similarity	NPC268736
0.8553	High Similarity	NPC476732
0.8553	High Similarity	NPC199965
0.8553	High Similarity	NPC472608
0.8533	High Similarity	NPC477933
0.8533	High Similarity	NPC477932
0.8519	High Similarity	NPC33768
0.8519	High Similarity	NPC269360
0.8519	High Similarity	NPC264005
0.8519	High Similarity	NPC252714
0.8514	High Similarity	NPC133922
0.8472	Intermediate Similarity	NPC324607
0.8472	Intermediate Similarity	NPC474962
0.8472	Intermediate Similarity	NPC321732
0.8462	Intermediate Similarity	NPC280781
0.8462	Intermediate Similarity	NPC469745
0.8462	Intermediate Similarity	NPC48756
0.8451	Intermediate Similarity	NPC41542
0.8451	Intermediate Similarity	NPC474221
0.8451	Intermediate Similarity	NPC478180
0.8451	Intermediate Similarity	NPC130459
0.8429	Intermediate Similarity	NPC230047
0.8429	Intermediate Similarity	NPC19311
0.8421	Intermediate Similarity	NPC477918
0.8421	Intermediate Similarity	NPC474404
0.8415	Intermediate Similarity	NPC16377
0.8415	Intermediate Similarity	NPC471900
0.8415	Intermediate Similarity	NPC474719
0.8415	Intermediate Similarity	NPC146937
0.8406	Intermediate Similarity	NPC114891
0.84	Intermediate Similarity	NPC477934
0.8378	Intermediate Similarity	NPC477229
0.8378	Intermediate Similarity	NPC282905
0.8378	Intermediate Similarity	NPC68426
0.8354	Intermediate Similarity	NPC268040
0.8333	Intermediate Similarity	NPC470609
0.8313	Intermediate Similarity	NPC24705
0.8313	Intermediate Similarity	NPC213832
0.8313	Intermediate Similarity	NPC220498
0.8313	Intermediate Similarity	NPC56962
0.8313	Intermediate Similarity	NPC57954
0.8312	Intermediate Similarity	NPC31031
0.8312	Intermediate Similarity	NPC243594
0.8312	Intermediate Similarity	NPC26029
0.831	Intermediate Similarity	NPC142712
0.8293	Intermediate Similarity	NPC142361
0.8293	Intermediate Similarity	NPC474684
0.8289	Intermediate Similarity	NPC471046
0.8267	Intermediate Similarity	NPC472854
0.8267	Intermediate Similarity	NPC159325
0.8267	Intermediate Similarity	NPC168511
0.8261	Intermediate Similarity	NPC71460
0.8261	Intermediate Similarity	NPC148174
0.8261	Intermediate Similarity	NPC218585
0.825	Intermediate Similarity	NPC475726
0.825	Intermediate Similarity	NPC245866
0.825	Intermediate Similarity	NPC327451
0.825	Intermediate Similarity	NPC472743
0.825	Intermediate Similarity	NPC471037
0.8243	Intermediate Similarity	NPC473267
0.8228	Intermediate Similarity	NPC476071
0.8214	Intermediate Similarity	NPC77756
0.8214	Intermediate Similarity	NPC169933
0.8205	Intermediate Similarity	NPC220379
0.8205	Intermediate Similarity	NPC472310
0.8194	Intermediate Similarity	NPC48079
0.8194	Intermediate Similarity	NPC475884
0.8194	Intermediate Similarity	NPC473230
0.8194	Intermediate Similarity	NPC472984
0.8193	Intermediate Similarity	NPC4309
0.8182	Intermediate Similarity	NPC264602
0.8182	Intermediate Similarity	NPC212453
0.8182	Intermediate Similarity	NPC471151
0.8171	Intermediate Similarity	NPC55309
0.8171	Intermediate Similarity	NPC28252
0.8169	Intermediate Similarity	NPC41577
0.8169	Intermediate Similarity	NPC473276
0.8169	Intermediate Similarity	NPC474380
0.8158	Intermediate Similarity	NPC27349
0.8158	Intermediate Similarity	NPC267753
0.8158	Intermediate Similarity	NPC24014
0.8148	Intermediate Similarity	NPC474482
0.8148	Intermediate Similarity	NPC74595
0.8148	Intermediate Similarity	NPC475745
0.8148	Intermediate Similarity	NPC50438
0.8148	Intermediate Similarity	NPC474996
0.8148	Intermediate Similarity	NPC473299
0.8148	Intermediate Similarity	NPC264665
0.8133	Intermediate Similarity	NPC81759
0.8125	Intermediate Similarity	NPC328007
0.8125	Intermediate Similarity	NPC317066
0.8125	Intermediate Similarity	NPC13494
0.8125	Intermediate Similarity	NPC477935
0.8118	Intermediate Similarity	NPC475416
0.8118	Intermediate Similarity	NPC52756
0.8108	Intermediate Similarity	NPC476731
0.8101	Intermediate Similarity	NPC472853
0.8095	Intermediate Similarity	NPC247312
0.8095	Intermediate Similarity	NPC474704
0.8095	Intermediate Similarity	NPC271974
0.8095	Intermediate Similarity	NPC475921
0.8082	Intermediate Similarity	NPC472741
0.8082	Intermediate Similarity	NPC473225
0.8077	Intermediate Similarity	NPC471045
0.8072	Intermediate Similarity	NPC187376
0.8072	Intermediate Similarity	NPC159046
0.8072	Intermediate Similarity	NPC233836
0.8056	Intermediate Similarity	NPC44122
0.8052	Intermediate Similarity	NPC108840
0.8049	Intermediate Similarity	NPC292553
0.8049	Intermediate Similarity	NPC62572
0.8049	Intermediate Similarity	NPC76518
0.8028	Intermediate Similarity	NPC159654
0.8028	Intermediate Similarity	NPC69149
0.8028	Intermediate Similarity	NPC281540
0.8028	Intermediate Similarity	NPC118937
0.8028	Intermediate Similarity	NPC167995
0.8026	Intermediate Similarity	NPC130011
0.8025	Intermediate Similarity	NPC259173
0.8023	Intermediate Similarity	NPC224060
0.8023	Intermediate Similarity	NPC473690
0.8023	Intermediate Similarity	NPC287118
0.8023	Intermediate Similarity	NPC244356
0.8023	Intermediate Similarity	NPC471902

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 NPC212733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	3312
0.2-0.3	3676
0.3-0.4	1118
0.4-0.5	270
0.5-0.6	210
0.6-0.7	167
0.7-0.8	17
0.8-0.85	5
0.85-0.9	11
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9857	High Similarity	NPD6117	Approved
0.9855	High Similarity	NPD6113	Clinical (unspecified phase)
0.9718	High Similarity	NPD6116	Phase 1
0.9583	High Similarity	NPD6118	Approved
0.9583	High Similarity	NPD6114	Approved
0.9583	High Similarity	NPD6115	Approved
0.9583	High Similarity	NPD6697	Approved
0.9286	High Similarity	NPD4809	Clinical (unspecified phase)
0.9286	High Similarity	NPD4808	Clinical (unspecified phase)
0.9	High Similarity	NPD3700	Clinical (unspecified phase)
0.9	High Similarity	NPD3699	Clinical (unspecified phase)
0.8734	High Similarity	NPD7520	Clinical (unspecified phase)
0.8649	High Similarity	NPD3703	Phase 2
0.8611	High Similarity	NPD4244	Approved
0.8611	High Similarity	NPD4789	Approved
0.8611	High Similarity	NPD4245	Approved
0.8592	High Similarity	NPD5360	Phase 3
0.8592	High Similarity	NPD5361	Clinical (unspecified phase)
0.8571	High Similarity	NPD4224	Phase 2
0.8493	Intermediate Similarity	NPD6081	Approved
0.8472	Intermediate Similarity	NPD3698	Phase 2
0.8429	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD5777	Approved
0.8158	Intermediate Similarity	NPD3702	Approved
0.8077	Intermediate Similarity	NPD3671	Phase 1
0.8	Intermediate Similarity	NPD4758	Discontinued
0.7973	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD8035	Phase 2
0.7907	Intermediate Similarity	NPD8034	Phase 2
0.7632	Intermediate Similarity	NPD4787	Phase 1
0.7625	Intermediate Similarity	NPD5364	Discontinued
0.75	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD8418	Phase 2
0.7471	Intermediate Similarity	NPD5328	Approved
0.7465	Intermediate Similarity	NPD3198	Approved
0.7381	Intermediate Similarity	NPD4788	Approved
0.7326	Intermediate Similarity	NPD3618	Phase 1
0.7303	Intermediate Similarity	NPD7515	Phase 2
0.7303	Intermediate Similarity	NPD6079	Approved
0.7262	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7033	Intermediate Similarity	NPD4202	Approved
0.7024	Intermediate Similarity	NPD7525	Registered
0.7024	Intermediate Similarity	NPD6928	Phase 2
0.7021	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7748	Approved
0.6947	Remote Similarity	NPD7639	Approved
0.6947	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD6675	Approved
0.6939	Remote Similarity	NPD6402	Approved
0.6939	Remote Similarity	NPD7128	Approved
0.6939	Remote Similarity	NPD5739	Approved
0.6897	Remote Similarity	NPD3133	Approved
0.6897	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD3666	Approved
0.6809	Remote Similarity	NPD4697	Phase 3
0.6809	Remote Similarity	NPD5222	Approved
0.6809	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5221	Approved
0.6804	Remote Similarity	NPD7632	Discontinued
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.68	Remote Similarity	NPD7320	Approved
0.6778	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD7521	Approved
0.6742	Remote Similarity	NPD7334	Approved
0.6742	Remote Similarity	NPD6409	Approved
0.6742	Remote Similarity	NPD6684	Approved
0.6742	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD7902	Approved
0.6737	Remote Similarity	NPD5173	Approved
0.6737	Remote Similarity	NPD4755	Approved
0.6737	Remote Similarity	NPD6084	Phase 2
0.6737	Remote Similarity	NPD6083	Phase 2
0.6733	Remote Similarity	NPD6372	Approved
0.6733	Remote Similarity	NPD6373	Approved
0.67	Remote Similarity	NPD5701	Approved
0.67	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD8298	Phase 2
0.6634	Remote Similarity	NPD6011	Approved
0.6627	Remote Similarity	NPD7339	Approved
0.6627	Remote Similarity	NPD6942	Approved
0.6602	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6869	Approved
0.6602	Remote Similarity	NPD8130	Phase 1
0.6602	Remote Similarity	NPD6617	Approved
0.6602	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6847	Approved
0.6602	Remote Similarity	NPD6649	Approved
0.6598	Remote Similarity	NPD5285	Approved
0.6598	Remote Similarity	NPD5286	Approved
0.6598	Remote Similarity	NPD4700	Approved
0.6598	Remote Similarity	NPD4696	Approved
0.6593	Remote Similarity	NPD6672	Approved
0.6593	Remote Similarity	NPD5737	Approved
0.6593	Remote Similarity	NPD6903	Approved
0.6588	Remote Similarity	NPD3617	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6556	Remote Similarity	NPD5279	Phase 3
0.6538	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD6882	Approved
0.6531	Remote Similarity	NPD5223	Approved
0.6528	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4753	Phase 2
0.6517	Remote Similarity	NPD3668	Phase 3
0.65	Remote Similarity	NPD6705	Phase 1
0.6477	Remote Similarity	NPD4223	Phase 3
0.6477	Remote Similarity	NPD4221	Approved
0.6465	Remote Similarity	NPD5225	Approved
0.6465	Remote Similarity	NPD4633	Approved
0.6465	Remote Similarity	NPD5224	Approved
0.6465	Remote Similarity	NPD5226	Approved
0.6465	Remote Similarity	NPD5211	Phase 2
0.6444	Remote Similarity	NPD5329	Approved
0.6436	Remote Similarity	NPD6920	Discontinued
0.6421	Remote Similarity	NPD7900	Approved
0.6421	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7909	Approved
0.64	Remote Similarity	NPD5174	Approved
0.64	Remote Similarity	NPD4754	Approved
0.64	Remote Similarity	NPD5175	Approved
0.6395	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6098	Approved
0.6364	Remote Similarity	NPD4139	Approved
0.6364	Remote Similarity	NPD4692	Approved
0.6355	Remote Similarity	NPD6940	Discontinued
0.6355	Remote Similarity	NPD6868	Approved
0.6354	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5695	Phase 3
0.6353	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5141	Approved
0.6333	Remote Similarity	NPD4197	Approved
0.6327	Remote Similarity	NPD5696	Approved
0.6322	Remote Similarity	NPD7645	Phase 2
0.6321	Remote Similarity	NPD4632	Approved
0.6321	Remote Similarity	NPD8133	Approved
0.6311	Remote Similarity	NPD6415	Discontinued
0.6296	Remote Similarity	NPD7115	Discovery
0.6277	Remote Similarity	NPD6700	Approved
0.6277	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4768	Approved
0.6275	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4748	Discontinued
0.6239	Remote Similarity	NPD6335	Approved
0.6232	Remote Similarity	NPD385	Approved
0.6232	Remote Similarity	NPD384	Approved
0.6211	Remote Similarity	NPD6703	Approved
0.6211	Remote Similarity	NPD5281	Approved
0.6211	Remote Similarity	NPD6702	Approved
0.6211	Remote Similarity	NPD5284	Approved
0.6207	Remote Similarity	NPD4802	Phase 2
0.6207	Remote Similarity	NPD4238	Approved
0.6204	Remote Similarity	NPD6274	Approved
0.62	Remote Similarity	NPD1700	Approved
0.6196	Remote Similarity	NPD4690	Approved
0.6196	Remote Similarity	NPD5205	Approved
0.6196	Remote Similarity	NPD4138	Approved
0.6196	Remote Similarity	NPD4688	Approved
0.6196	Remote Similarity	NPD4689	Approved
0.6196	Remote Similarity	NPD4693	Phase 3
0.6186	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5210	Approved
0.6182	Remote Similarity	NPD7100	Approved
0.6182	Remote Similarity	NPD7101	Approved
0.617	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6080	Approved
0.617	Remote Similarity	NPD6904	Approved
0.617	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD5168	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6009	Approved
0.6147	Remote Similarity	NPD6317	Approved
0.6146	Remote Similarity	NPD8171	Discontinued
0.6118	Remote Similarity	NPD6926	Approved
0.6118	Remote Similarity	NPD6924	Approved
0.6117	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6313	Approved
0.6091	Remote Similarity	NPD6314	Approved
0.6087	Remote Similarity	NPD634	Phase 3
0.6082	Remote Similarity	NPD6001	Approved
0.6071	Remote Similarity	NPD6908	Approved
0.6071	Remote Similarity	NPD6909	Approved
0.6064	Remote Similarity	NPD5208	Approved
0.6049	Remote Similarity	NPD375	Phase 2
0.6042	Remote Similarity	NPD6411	Approved
0.6038	Remote Similarity	NPD5135	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