NPASS Compound

Structure

NPC473172 OpenBabel07101718192D 35 38 0 0 1 0 0 0 0 0999 V2000 0.5758 -2.9262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8881 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8625 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0136 -2.5088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8111 -3.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3963 0.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1808 -2.4047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2278 -2.2021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4819 -3.3314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4994 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4350 -3.5340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0870 -2.8099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8300 -4.0555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4737 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0629 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7361 -4.4606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7859 -1.8832 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 0 0 0 0 17 1 1 1 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 1 0 0 0 20 24 1 0 0 0 0 20 32 2 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 27 35 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	526.615
LogP:	3.265
LogD:	3.099
LogS:	-4.331
# Rotatable Bonds:	5
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	5.185
Fsp3:	0.8
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:	-5.215
MDCK Permeability:	2.9638362320838496e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.18
30% Bioavailability (F30%):	0.805

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.733
Plasma Protein Binding (PPB):	92.4143295288086%
Volume Distribution (VD):	0.868
Pgp-substrate:	6.483460903167725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	6.227
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.748
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.164
Carcinogencity:	0.636
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC473172

Natural Product ID:	NPC473172
*Common Name:**	PGQUPZCFLHXEHV-KPYCMCGFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PGQUPZCFLHXEHV-KPYCMCGFSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-17(15-19(31)25(34)27(4,5)35)24-18-9-10-22-28(6)13-12-23(33)26(2,3)21(28)11-14-29(22,7)30(18,8)16-20(24)32/h9-10,17,19,21-22,25,31,34-35H,11-16H2,1-8H3/t17-,19+,21+,22+,25+,28+,29+,30+/m1/s1
SMILES:	O[C@H]([C@@H](C(O)(C)C)O)C[C@H](C1=C2C=C[C@@H]3[C@]([C@]2(CC1=O)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632953
PubChem CID:	n.a.
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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	22740.0	nM	PMID[555309]

☑ 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 NPC473172 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	186
0.1-0.2	959
0.2-0.3	4085
0.3-0.4	10222
0.4-0.5	12732
0.5-0.6	7189
0.6-0.7	5543
0.7-0.8	1668
0.8-0.85	100
0.85-0.9	7
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC473164
0.9333	High Similarity	NPC473162
0.9255	High Similarity	NPC473163
0.9231	High Similarity	NPC473170
0.9032	High Similarity	NPC473161
0.8901	High Similarity	NPC19114
0.8876	High Similarity	NPC90652
0.8778	High Similarity	NPC44181
0.8778	High Similarity	NPC470417
0.8764	High Similarity	NPC473168
0.8696	High Similarity	NPC473167
0.8636	High Similarity	NPC86370
0.8632	High Similarity	NPC474785
0.8632	High Similarity	NPC474938
0.8571	High Similarity	NPC292491
0.8571	High Similarity	NPC310752
0.8557	High Similarity	NPC473174
0.8556	High Similarity	NPC89077
0.8542	High Similarity	NPC471582
0.8539	High Similarity	NPC214043
0.8539	High Similarity	NPC85774
0.8478	Intermediate Similarity	NPC32830
0.8478	Intermediate Similarity	NPC477943
0.8478	Intermediate Similarity	NPC1015
0.8478	Intermediate Similarity	NPC31985
0.8462	Intermediate Similarity	NPC141292
0.8462	Intermediate Similarity	NPC136548
0.8462	Intermediate Similarity	NPC58063
0.8444	Intermediate Similarity	NPC469948
0.8421	Intermediate Similarity	NPC280725
0.8421	Intermediate Similarity	NPC180950
0.8409	Intermediate Similarity	NPC121984
0.8404	Intermediate Similarity	NPC472930
0.8404	Intermediate Similarity	NPC474736
0.8404	Intermediate Similarity	NPC474807
0.8387	Intermediate Similarity	NPC129913
0.837	Intermediate Similarity	NPC328539
0.837	Intermediate Similarity	NPC158778
0.8352	Intermediate Similarity	NPC474732
0.8352	Intermediate Similarity	NPC145879
0.8352	Intermediate Similarity	NPC31564
0.8352	Intermediate Similarity	NPC327115
0.8352	Intermediate Similarity	NPC474733
0.8352	Intermediate Similarity	NPC474778
0.8351	Intermediate Similarity	NPC471717
0.8333	Intermediate Similarity	NPC329043
0.8333	Intermediate Similarity	NPC58841
0.8333	Intermediate Similarity	NPC161423
0.8333	Intermediate Similarity	NPC227064
0.8333	Intermediate Similarity	NPC471463
0.8333	Intermediate Similarity	NPC321187
0.8333	Intermediate Similarity	NPC473246
0.8333	Intermediate Similarity	NPC249954
0.8316	Intermediate Similarity	NPC472977
0.8316	Intermediate Similarity	NPC8993
0.8316	Intermediate Similarity	NPC474690
0.8316	Intermediate Similarity	NPC67831
0.8316	Intermediate Similarity	NPC174051
0.8316	Intermediate Similarity	NPC299100
0.8316	Intermediate Similarity	NPC472976
0.8316	Intermediate Similarity	NPC471207
0.8315	Intermediate Similarity	NPC212083
0.8298	Intermediate Similarity	NPC262870
0.8298	Intermediate Similarity	NPC475806
0.8298	Intermediate Similarity	NPC155304
0.8298	Intermediate Similarity	NPC185936
0.8298	Intermediate Similarity	NPC472978
0.8298	Intermediate Similarity	NPC168027
0.8295	Intermediate Similarity	NPC2482
0.8283	Intermediate Similarity	NPC477915
0.8283	Intermediate Similarity	NPC87351
0.828	Intermediate Similarity	NPC86319
0.828	Intermediate Similarity	NPC326627
0.828	Intermediate Similarity	NPC186688
0.828	Intermediate Similarity	NPC310010
0.828	Intermediate Similarity	NPC275740
0.8265	Intermediate Similarity	NPC144956
0.8261	Intermediate Similarity	NPC93778
0.8261	Intermediate Similarity	NPC241875
0.8261	Intermediate Similarity	NPC475740
0.8261	Intermediate Similarity	NPC99909
0.8261	Intermediate Similarity	NPC469314
0.8261	Intermediate Similarity	NPC469317
0.8247	Intermediate Similarity	NPC161147
0.8247	Intermediate Similarity	NPC18509
0.8242	Intermediate Similarity	NPC470574
0.8229	Intermediate Similarity	NPC472932
0.8229	Intermediate Similarity	NPC259286
0.8229	Intermediate Similarity	NPC88310
0.8222	Intermediate Similarity	NPC64600
0.8211	Intermediate Similarity	NPC134826
0.82	Intermediate Similarity	NPC264048
0.82	Intermediate Similarity	NPC475050
0.82	Intermediate Similarity	NPC311612
0.82	Intermediate Similarity	NPC239716
0.8191	Intermediate Similarity	NPC85173
0.8191	Intermediate Similarity	NPC320026
0.8191	Intermediate Similarity	NPC171441
0.8182	Intermediate Similarity	NPC474113
0.8172	Intermediate Similarity	NPC131470
0.8172	Intermediate Similarity	NPC143767
0.8161	Intermediate Similarity	NPC325946
0.8155	Intermediate Similarity	NPC41405
0.8155	Intermediate Similarity	NPC214644
0.8152	Intermediate Similarity	NPC118648
0.8152	Intermediate Similarity	NPC222613
0.8152	Intermediate Similarity	NPC94666
0.8152	Intermediate Similarity	NPC475022
0.8144	Intermediate Similarity	NPC49371
0.8144	Intermediate Similarity	NPC471153
0.8144	Intermediate Similarity	NPC473158
0.8137	Intermediate Similarity	NPC83744
0.8137	Intermediate Similarity	NPC477916
0.8137	Intermediate Similarity	NPC473169
0.8132	Intermediate Similarity	NPC59453
0.8132	Intermediate Similarity	NPC82902
0.8132	Intermediate Similarity	NPC221758
0.8132	Intermediate Similarity	NPC237712
0.8132	Intermediate Similarity	NPC473157
0.8132	Intermediate Similarity	NPC476412
0.8125	Intermediate Similarity	NPC49670
0.8119	Intermediate Similarity	NPC473175
0.8119	Intermediate Similarity	NPC255309
0.8119	Intermediate Similarity	NPC209502
0.8119	Intermediate Similarity	NPC204833
0.8111	Intermediate Similarity	NPC151519
0.8105	Intermediate Similarity	NPC131872
0.8105	Intermediate Similarity	NPC272746
0.8105	Intermediate Similarity	NPC473998
0.81	Intermediate Similarity	NPC473424
0.81	Intermediate Similarity	NPC473928
0.8085	Intermediate Similarity	NPC473999
0.8085	Intermediate Similarity	NPC2983
0.8085	Intermediate Similarity	NPC250592
0.8085	Intermediate Similarity	NPC469319
0.8085	Intermediate Similarity	NPC474245
0.8085	Intermediate Similarity	NPC472973
0.8085	Intermediate Similarity	NPC229871
0.8085	Intermediate Similarity	NPC119416
0.8085	Intermediate Similarity	NPC268406
0.8085	Intermediate Similarity	NPC26959
0.8085	Intermediate Similarity	NPC77263
0.8085	Intermediate Similarity	NPC309603
0.8081	Intermediate Similarity	NPC474720
0.8081	Intermediate Similarity	NPC316964
0.8077	Intermediate Similarity	NPC5284
0.8065	Intermediate Similarity	NPC317590
0.8065	Intermediate Similarity	NPC287079
0.8065	Intermediate Similarity	NPC469322
0.8058	Intermediate Similarity	NPC329417
0.8043	Intermediate Similarity	NPC474218
0.8043	Intermediate Similarity	NPC476426
0.8043	Intermediate Similarity	NPC471224
0.8041	Intermediate Similarity	NPC200702
0.8041	Intermediate Similarity	NPC472824
0.8041	Intermediate Similarity	NPC139459
0.8039	Intermediate Similarity	NPC214264
0.8039	Intermediate Similarity	NPC97202
0.8039	Intermediate Similarity	NPC260268
0.8039	Intermediate Similarity	NPC150531
0.8039	Intermediate Similarity	NPC48733
0.8039	Intermediate Similarity	NPC149047
0.8039	Intermediate Similarity	NPC476027
0.8039	Intermediate Similarity	NPC50692
0.8039	Intermediate Similarity	NPC319077
0.8039	Intermediate Similarity	NPC202167
0.8039	Intermediate Similarity	NPC296945
0.8039	Intermediate Similarity	NPC171137
0.8039	Intermediate Similarity	NPC152695
0.8039	Intermediate Similarity	NPC49958
0.8039	Intermediate Similarity	NPC85829
0.8039	Intermediate Similarity	NPC96377
0.8039	Intermediate Similarity	NPC302607
0.8022	Intermediate Similarity	NPC476082
0.8022	Intermediate Similarity	NPC278648
0.8021	Intermediate Similarity	NPC475255
0.8021	Intermediate Similarity	NPC472942
0.8021	Intermediate Similarity	NPC69454
0.8021	Intermediate Similarity	NPC109305
0.8021	Intermediate Similarity	NPC233118
0.8021	Intermediate Similarity	NPC250575
0.802	Intermediate Similarity	NPC117185
0.802	Intermediate Similarity	NPC191892
0.802	Intermediate Similarity	NPC111323
0.8	Intermediate Similarity	NPC183283
0.8	Intermediate Similarity	NPC48010
0.8	Intermediate Similarity	NPC282524
0.8	Intermediate Similarity	NPC126993
0.8	Intermediate Similarity	NPC289213
0.798	Intermediate Similarity	NPC103051
0.798	Intermediate Similarity	NPC114274
0.798	Intermediate Similarity	NPC191565
0.7979	Intermediate Similarity	NPC53911
0.7979	Intermediate Similarity	NPC471722
0.7961	Intermediate Similarity	NPC58370
0.7961	Intermediate Similarity	NPC220229
0.7961	Intermediate Similarity	NPC329048
0.7961	Intermediate Similarity	NPC475060
0.7961	Intermediate Similarity	NPC43285
0.7961	Intermediate Similarity	NPC330011

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 NPC473172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1190
0.2-0.3	3684
0.3-0.4	2732
0.4-0.5	887
0.5-0.6	194
0.6-0.7	166
0.7-0.8	122
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD6079	Approved
0.8478	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD3666	Approved
0.8333	Intermediate Similarity	NPD3665	Phase 1
0.8333	Intermediate Similarity	NPD3133	Approved
0.828	Intermediate Similarity	NPD4753	Phase 2
0.8265	Intermediate Similarity	NPD4696	Approved
0.8265	Intermediate Similarity	NPD5286	Approved
0.8265	Intermediate Similarity	NPD5285	Approved
0.8247	Intermediate Similarity	NPD4755	Approved
0.8152	Intermediate Similarity	NPD5279	Phase 3
0.8152	Intermediate Similarity	NPD3618	Phase 1
0.8144	Intermediate Similarity	NPD5222	Approved
0.8144	Intermediate Similarity	NPD5221	Approved
0.8144	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD4786	Approved
0.8111	Intermediate Similarity	NPD3667	Approved
0.81	Intermediate Similarity	NPD4633	Approved
0.81	Intermediate Similarity	NPD5224	Approved
0.81	Intermediate Similarity	NPD5225	Approved
0.81	Intermediate Similarity	NPD5226	Approved
0.81	Intermediate Similarity	NPD5211	Phase 2
0.8081	Intermediate Similarity	NPD4700	Approved
0.8061	Intermediate Similarity	NPD5173	Approved
0.8041	Intermediate Similarity	NPD5210	Approved
0.8041	Intermediate Similarity	NPD4629	Approved
0.802	Intermediate Similarity	NPD5175	Approved
0.802	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5223	Approved
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7941	Intermediate Similarity	NPD5141	Approved
0.7912	Intermediate Similarity	NPD4223	Phase 3
0.7912	Intermediate Similarity	NPD4221	Approved
0.7905	Intermediate Similarity	NPD4634	Approved
0.7885	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD6881	Approved
0.7879	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD6083	Phase 2
0.7864	Intermediate Similarity	NPD6675	Approved
0.7864	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD7128	Approved
0.7864	Intermediate Similarity	NPD5739	Approved
0.7849	Intermediate Similarity	NPD5329	Approved
0.7835	Intermediate Similarity	NPD4202	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7766	Intermediate Similarity	NPD5280	Approved
0.7766	Intermediate Similarity	NPD4519	Discontinued
0.7766	Intermediate Similarity	NPD4623	Approved
0.7766	Intermediate Similarity	NPD4694	Approved
0.7757	Intermediate Similarity	NPD8297	Approved
0.7742	Intermediate Similarity	NPD4197	Approved
0.7736	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD6883	Approved
0.7736	Intermediate Similarity	NPD7290	Approved
0.7732	Intermediate Similarity	NPD5281	Approved
0.7732	Intermediate Similarity	NPD7515	Phase 2
0.7732	Intermediate Similarity	NPD5284	Approved
0.7714	Intermediate Similarity	NPD4730	Approved
0.7714	Intermediate Similarity	NPD4729	Approved
0.7714	Intermediate Similarity	NPD7320	Approved
0.7692	Intermediate Similarity	NPD4768	Approved
0.7692	Intermediate Similarity	NPD4767	Approved
0.767	Intermediate Similarity	NPD4754	Approved
0.7664	Intermediate Similarity	NPD6847	Approved
0.7664	Intermediate Similarity	NPD6649	Approved
0.7664	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6617	Approved
0.7664	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6012	Approved
0.7642	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD6373	Approved
0.7642	Intermediate Similarity	NPD6372	Approved
0.7642	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD5701	Approved
0.7593	Intermediate Similarity	NPD6882	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD4693	Phase 3
0.7579	Intermediate Similarity	NPD6684	Approved
0.7579	Intermediate Similarity	NPD5205	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD4138	Approved
0.7579	Intermediate Similarity	NPD4688	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5690	Phase 2
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD4690	Approved
0.7579	Intermediate Similarity	NPD4689	Approved
0.757	Intermediate Similarity	NPD5248	Approved
0.757	Intermediate Similarity	NPD5250	Approved
0.757	Intermediate Similarity	NPD5251	Approved
0.757	Intermediate Similarity	NPD5247	Approved
0.757	Intermediate Similarity	NPD5249	Phase 3
0.7553	Intermediate Similarity	NPD3668	Phase 3
0.7551	Intermediate Similarity	NPD6411	Approved
0.7547	Intermediate Similarity	NPD5128	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD5217	Approved
0.7475	Intermediate Similarity	NPD6399	Phase 3
0.7473	Intermediate Similarity	NPD3617	Approved
0.7451	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD4788	Approved
0.7444	Intermediate Similarity	NPD6933	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.7416	Intermediate Similarity	NPD4058	Approved
0.7407	Intermediate Similarity	NPD5135	Approved
0.7407	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5169	Approved
0.74	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD4195	Approved
0.7383	Intermediate Similarity	NPD5168	Approved
0.7347	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6101	Approved
0.7339	Intermediate Similarity	NPD5127	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7281	Intermediate Similarity	NPD6319	Approved
0.7281	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD4096	Approved
0.7245	Intermediate Similarity	NPD4518	Approved
0.7222	Intermediate Similarity	NPD4687	Approved
0.7222	Intermediate Similarity	NPD5733	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.72	Intermediate Similarity	NPD6050	Approved
0.72	Intermediate Similarity	NPD5694	Approved
0.7193	Intermediate Similarity	NPD7101	Approved
0.7193	Intermediate Similarity	NPD7100	Approved
0.7184	Intermediate Similarity	NPD7902	Approved
0.7172	Intermediate Similarity	NPD6904	Approved
0.7172	Intermediate Similarity	NPD6673	Approved
0.7172	Intermediate Similarity	NPD6080	Approved
0.7168	Intermediate Similarity	NPD6009	Approved
0.7159	Intermediate Similarity	NPD4137	Phase 3
0.7155	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.713	Intermediate Similarity	NPD6059	Approved
0.7129	Intermediate Similarity	NPD5133	Approved
0.7128	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7525	Registered
0.7105	Intermediate Similarity	NPD6335	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.71	Intermediate Similarity	NPD5207	Approved
0.708	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7079	Intermediate Similarity	NPD4747	Approved
0.7079	Intermediate Similarity	NPD4691	Approved
0.7069	Intermediate Similarity	NPD6015	Approved
0.7069	Intermediate Similarity	NPD6016	Approved
0.7065	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4522	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.7018	Intermediate Similarity	NPD6317	Approved
0.7011	Intermediate Similarity	NPD7331	Phase 2
0.7009	Intermediate Similarity	NPD5988	Approved
0.7	Intermediate Similarity	NPD5276	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6932	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.697	Remote Similarity	NPD7524	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6947	Remote Similarity	NPD7509	Discontinued
0.6947	Remote Similarity	NPD6931	Approved
0.6947	Remote Similarity	NPD7332	Phase 2
0.6947	Remote Similarity	NPD5368	Approved
0.6947	Remote Similarity	NPD6930	Phase 2
0.6939	Remote Similarity	NPD1696	Phase 3
0.6939	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD7078	Approved
0.6916	Remote Similarity	NPD5091	Approved
0.6915	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6686	Approved
0.6907	Remote Similarity	NPD6695	Phase 3
0.69	Remote Similarity	NPD5208	Approved
0.6897	Remote Similarity	NPD7341	Phase 2
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data