NPASS Compound

Structure

NPC473168 OpenBabel07101718292D 33 36 0 0 1 0 0 0 0 0999 V2000 -3.0203 -2.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8099 -5.1553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0868 -5.8064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 0.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4176 -3.4085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7183 -4.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3399 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7680 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0686 -2.6855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7680 -1.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0672 -5.0569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1155 -4.8547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 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 4.2131 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 -5.9823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1852 -3.9293 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 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 23 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 20 19 1 1 0 0 0 20 21 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 2 0 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 27 33 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	5.296
LogD:	4.046
LogS:	-4.008
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	4.967
Fsp3:	0.833
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:	-5.052
MDCK Permeability:	1.6217923985095695e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	93.4142837524414%
Volume Distribution (VD):	0.988
Pgp-substrate:	3.3285744190216064%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.353
CYP3A4-substrate:	0.937

ADMET: Excretion

Clearance (CL):	7.832
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.151
Carcinogencity:	0.565
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC473168

Natural Product ID:	NPC473168
*Common Name:**	OKSOIVLQNAAMNU-QXGHGRIXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OKSOIVLQNAAMNU-QXGHGRIXSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19(9-12-25(32)27(4,5)33)20-13-17-29(7)21(20)10-11-23-28(6)16-15-24(31)26(2,3)22(28)14-18-30(23,29)8/h10-11,19-20,22,25,32-33H,9,12-18H2,1-8H3/t19-,20-,22+,25+,28+,29+,30+/m1/s1
SMILES:	CC(CCC(C(C)(C)O)O)C1CCC2(C1=CC=C3C2(CCC4C3(CCC(=O)C4(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632948
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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	4580.0	nM	PMID[489842]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	140.0	nM	PMID[489843]

☑ 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 NPC473168 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	159
0.1-0.2	936
0.2-0.3	4526
0.3-0.4	14690
0.4-0.5	8451
0.5-0.6	6507
0.6-0.7	5072
0.7-0.8	2079
0.8-0.85	191
0.85-0.9	74
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC89077
0.9398	High Similarity	NPC90652
0.9286	High Similarity	NPC470417
0.9286	High Similarity	NPC44181
0.9176	High Similarity	NPC32830
0.9036	High Similarity	NPC82902
0.9036	High Similarity	NPC221758
0.9036	High Similarity	NPC85774
0.9036	High Similarity	NPC59453
0.9036	High Similarity	NPC214043
0.8966	High Similarity	NPC262870
0.8929	High Similarity	NPC471224
0.8929	High Similarity	NPC474218
0.8875	High Similarity	NPC325946
0.8824	High Similarity	NPC31564
0.8824	High Similarity	NPC474732
0.8824	High Similarity	NPC469994
0.8824	High Similarity	NPC474733
0.8824	High Similarity	NPC474778
0.8824	High Similarity	NPC145879
0.8824	High Similarity	NPC51014
0.881	High Similarity	NPC473246
0.8795	High Similarity	NPC151519
0.8795	High Similarity	NPC212083
0.878	High Similarity	NPC472478
0.8764	High Similarity	NPC67831
0.8764	High Similarity	NPC473172
0.8764	High Similarity	NPC174051
0.875	High Similarity	NPC19114
0.8736	High Similarity	NPC2983
0.8736	High Similarity	NPC474245
0.8736	High Similarity	NPC76879
0.8721	High Similarity	NPC317590
0.8721	High Similarity	NPC136548
0.8721	High Similarity	NPC58063
0.8721	High Similarity	NPC475740
0.8706	High Similarity	NPC474083
0.8706	High Similarity	NPC469948
0.8675	High Similarity	NPC121984
0.8659	High Similarity	NPC474113
0.8659	High Similarity	NPC215843
0.8652	High Similarity	NPC474736
0.8636	High Similarity	NPC69622
0.8636	High Similarity	NPC320026
0.8636	High Similarity	NPC171441
0.8621	High Similarity	NPC193360
0.8621	High Similarity	NPC328313
0.8605	High Similarity	NPC155011
0.8588	High Similarity	NPC58841
0.8588	High Similarity	NPC237712
0.8588	High Similarity	NPC161423
0.8588	High Similarity	NPC227064
0.8588	High Similarity	NPC321187
0.8588	High Similarity	NPC329043
0.8571	High Similarity	NPC473164
0.8554	High Similarity	NPC2482
0.8539	High Similarity	NPC189520
0.8539	High Similarity	NPC475806
0.8539	High Similarity	NPC473167
0.8537	High Similarity	NPC82635
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC473999
0.8523	High Similarity	NPC1015
0.8523	High Similarity	NPC215029
0.8523	High Similarity	NPC186688
0.8523	High Similarity	NPC31985
0.8523	High Similarity	NPC102414
0.8523	High Similarity	NPC84271
0.8523	High Similarity	NPC26959
0.8523	High Similarity	NPC476733
0.8523	High Similarity	NPC477943
0.8523	High Similarity	NPC309603
0.8523	High Similarity	NPC268406
0.8506	High Similarity	NPC138756
0.8506	High Similarity	NPC142361
0.8506	High Similarity	NPC141292
0.8506	High Similarity	NPC93778
0.8506	High Similarity	NPC99909
0.8506	High Similarity	NPC474684
0.8506	High Similarity	NPC96496
0.8488	Intermediate Similarity	NPC470574
0.8478	Intermediate Similarity	NPC473161
0.8471	Intermediate Similarity	NPC69279
0.8471	Intermediate Similarity	NPC83569
0.8471	Intermediate Similarity	NPC86370
0.8471	Intermediate Similarity	NPC476082
0.8471	Intermediate Similarity	NPC278648
0.8452	Intermediate Similarity	NPC147066
0.8452	Intermediate Similarity	NPC3915
0.8444	Intermediate Similarity	NPC472942
0.8444	Intermediate Similarity	NPC152897
0.8444	Intermediate Similarity	NPC250575
0.8444	Intermediate Similarity	NPC66429
0.8434	Intermediate Similarity	NPC328714
0.8434	Intermediate Similarity	NPC472490
0.8427	Intermediate Similarity	NPC48010
0.8409	Intermediate Similarity	NPC310752
0.8409	Intermediate Similarity	NPC292491
0.8409	Intermediate Similarity	NPC471722
0.8409	Intermediate Similarity	NPC53911
0.8409	Intermediate Similarity	NPC328539
0.8391	Intermediate Similarity	NPC475022
0.8391	Intermediate Similarity	NPC20688
0.8391	Intermediate Similarity	NPC72133
0.8391	Intermediate Similarity	NPC327115
0.8391	Intermediate Similarity	NPC222613
0.8391	Intermediate Similarity	NPC324063
0.8391	Intermediate Similarity	NPC118648
0.8391	Intermediate Similarity	NPC94755
0.8372	Intermediate Similarity	NPC165064
0.8372	Intermediate Similarity	NPC473157
0.8372	Intermediate Similarity	NPC472265
0.8372	Intermediate Similarity	NPC180834
0.837	Intermediate Similarity	NPC155676
0.8353	Intermediate Similarity	NPC145143
0.8353	Intermediate Similarity	NPC310989
0.8353	Intermediate Similarity	NPC48362
0.8353	Intermediate Similarity	NPC193347
0.8352	Intermediate Similarity	NPC8993
0.8352	Intermediate Similarity	NPC473162
0.8352	Intermediate Similarity	NPC49670
0.8352	Intermediate Similarity	NPC209662
0.8333	Intermediate Similarity	NPC272746
0.8333	Intermediate Similarity	NPC154101
0.8333	Intermediate Similarity	NPC473998
0.8315	Intermediate Similarity	NPC475921
0.8315	Intermediate Similarity	NPC86319
0.8315	Intermediate Similarity	NPC310010
0.8315	Intermediate Similarity	NPC474704
0.8315	Intermediate Similarity	NPC275740
0.8315	Intermediate Similarity	NPC326627
0.8298	Intermediate Similarity	NPC167974
0.8295	Intermediate Similarity	NPC187376
0.8295	Intermediate Similarity	NPC233836
0.8295	Intermediate Similarity	NPC159046
0.8295	Intermediate Similarity	NPC472481
0.8295	Intermediate Similarity	NPC472482
0.8295	Intermediate Similarity	NPC472484
0.8293	Intermediate Similarity	NPC315261
0.828	Intermediate Similarity	NPC472074
0.828	Intermediate Similarity	NPC472073
0.828	Intermediate Similarity	NPC474938
0.828	Intermediate Similarity	NPC474785
0.8276	Intermediate Similarity	NPC274724
0.8276	Intermediate Similarity	NPC202868
0.8276	Intermediate Similarity	NPC470048
0.8276	Intermediate Similarity	NPC133954
0.8261	Intermediate Similarity	NPC127063
0.8261	Intermediate Similarity	NPC473170
0.8261	Intermediate Similarity	NPC263347
0.8261	Intermediate Similarity	NPC271195
0.8256	Intermediate Similarity	NPC470046
0.8256	Intermediate Similarity	NPC470047
0.8242	Intermediate Similarity	NPC109305
0.8242	Intermediate Similarity	NPC474807
0.8242	Intermediate Similarity	NPC475255
0.8235	Intermediate Similarity	NPC6707
0.8235	Intermediate Similarity	NPC4166
0.8235	Intermediate Similarity	NPC14151
0.8235	Intermediate Similarity	NPC201912
0.8235	Intermediate Similarity	NPC142244
0.8235	Intermediate Similarity	NPC38350
0.8222	Intermediate Similarity	NPC289213
0.8222	Intermediate Similarity	NPC85173
0.8222	Intermediate Similarity	NPC191684
0.8222	Intermediate Similarity	NPC129913
0.8222	Intermediate Similarity	NPC136801
0.8222	Intermediate Similarity	NPC126993
0.8214	Intermediate Similarity	NPC201459
0.8214	Intermediate Similarity	NPC477371
0.8211	Intermediate Similarity	NPC473174
0.8202	Intermediate Similarity	NPC143767
0.8202	Intermediate Similarity	NPC471724
0.8202	Intermediate Similarity	NPC131470
0.8193	Intermediate Similarity	NPC198968
0.8193	Intermediate Similarity	NPC318495
0.8193	Intermediate Similarity	NPC155986
0.8193	Intermediate Similarity	NPC106078
0.8193	Intermediate Similarity	NPC149249
0.8191	Intermediate Similarity	NPC103051
0.8191	Intermediate Similarity	NPC191565
0.8182	Intermediate Similarity	NPC73038
0.8182	Intermediate Similarity	NPC213412
0.8182	Intermediate Similarity	NPC475862
0.8182	Intermediate Similarity	NPC74363
0.8182	Intermediate Similarity	NPC28252
0.8182	Intermediate Similarity	NPC55309
0.8182	Intermediate Similarity	NPC470955
0.8172	Intermediate Similarity	NPC471463
0.8172	Intermediate Similarity	NPC49371
0.8172	Intermediate Similarity	NPC78473
0.8171	Intermediate Similarity	NPC114236
0.8161	Intermediate Similarity	NPC476412
0.8161	Intermediate Similarity	NPC144258
0.8161	Intermediate Similarity	NPC33913
0.8152	Intermediate Similarity	NPC196485
0.8152	Intermediate Similarity	NPC292793
0.8152	Intermediate Similarity	NPC245972
0.8152	Intermediate Similarity	NPC111015
0.8152	Intermediate Similarity	NPC469406

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 NPC473168 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1168
0.2-0.3	3899
0.3-0.4	2703
0.4-0.5	725
0.5-0.6	200
0.6-0.7	118
0.7-0.8	160
0.8-0.85	23
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9036	High Similarity	NPD4786	Approved
0.8795	High Similarity	NPD3667	Approved
0.8605	High Similarity	NPD5279	Phase 3
0.8588	High Similarity	NPD3666	Approved
0.8588	High Similarity	NPD3665	Phase 1
0.8588	High Similarity	NPD3133	Approved
0.8523	High Similarity	NPD5328	Approved
0.8391	Intermediate Similarity	NPD3618	Phase 1
0.8353	Intermediate Similarity	NPD4223	Phase 3
0.8353	Intermediate Similarity	NPD4221	Approved
0.8333	Intermediate Similarity	NPD6079	Approved
0.8315	Intermediate Similarity	NPD4753	Phase 2
0.8293	Intermediate Similarity	NPD6933	Approved
0.8276	Intermediate Similarity	NPD5329	Approved
0.8242	Intermediate Similarity	NPD4202	Approved
0.8182	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4694	Approved
0.8161	Intermediate Similarity	NPD4197	Approved
0.8049	Intermediate Similarity	NPD6926	Approved
0.8049	Intermediate Similarity	NPD6924	Approved
0.8046	Intermediate Similarity	NPD4788	Approved
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.7978	Intermediate Similarity	NPD4689	Approved
0.7978	Intermediate Similarity	NPD5205	Approved
0.7978	Intermediate Similarity	NPD4138	Approved
0.7978	Intermediate Similarity	NPD4693	Phase 3
0.7978	Intermediate Similarity	NPD4690	Approved
0.7978	Intermediate Similarity	NPD4688	Approved
0.7955	Intermediate Similarity	NPD3668	Phase 3
0.7952	Intermediate Similarity	NPD6942	Approved
0.7952	Intermediate Similarity	NPD7339	Approved
0.7895	Intermediate Similarity	NPD4755	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7872	Intermediate Similarity	NPD5210	Approved
0.7872	Intermediate Similarity	NPD4629	Approved
0.7789	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5222	Approved
0.7789	Intermediate Similarity	NPD4697	Phase 3
0.7789	Intermediate Similarity	NPD5221	Approved
0.7778	Intermediate Similarity	NPD7146	Approved
0.7778	Intermediate Similarity	NPD6684	Approved
0.7778	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD6409	Approved
0.7778	Intermediate Similarity	NPD5330	Approved
0.7778	Intermediate Similarity	NPD7521	Approved
0.7778	Intermediate Similarity	NPD7334	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD7515	Phase 2
0.7742	Intermediate Similarity	NPD5284	Approved
0.7732	Intermediate Similarity	NPD4700	Approved
0.7732	Intermediate Similarity	NPD4696	Approved
0.7732	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5286	Approved
0.7708	Intermediate Similarity	NPD5173	Approved
0.7701	Intermediate Similarity	NPD7525	Registered
0.7674	Intermediate Similarity	NPD3617	Approved
0.7667	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5223	Approved
0.7647	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4096	Approved
0.7619	Intermediate Similarity	NPD5733	Approved
0.7614	Intermediate Similarity	NPD4692	Approved
0.7614	Intermediate Similarity	NPD4139	Approved
0.7609	Intermediate Similarity	NPD6903	Approved
0.7609	Intermediate Similarity	NPD5737	Approved
0.7609	Intermediate Similarity	NPD6672	Approved
0.7609	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4243	Approved
0.7586	Intermediate Similarity	NPD4195	Approved
0.7582	Intermediate Similarity	NPD4623	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7582	Intermediate Similarity	NPD4519	Discontinued
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD5226	Approved
0.7576	Intermediate Similarity	NPD5224	Approved
0.7576	Intermediate Similarity	NPD4633	Approved
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7561	Intermediate Similarity	NPD6922	Approved
0.7561	Intermediate Similarity	NPD6923	Approved
0.7525	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD5739	Approved
0.7525	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD6930	Phase 2
0.75	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7474	Intermediate Similarity	NPD5133	Approved
0.747	Intermediate Similarity	NPD4747	Approved
0.747	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.7451	Intermediate Similarity	NPD6412	Phase 2
0.7449	Intermediate Similarity	NPD5696	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7412	Intermediate Similarity	NPD4687	Approved
0.7412	Intermediate Similarity	NPD4785	Approved
0.7412	Intermediate Similarity	NPD4784	Approved
0.7412	Intermediate Similarity	NPD4058	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7396	Intermediate Similarity	NPD7748	Approved
0.7386	Intermediate Similarity	NPD6929	Approved
0.7381	Intermediate Similarity	NPD5276	Approved
0.7381	Intermediate Similarity	NPD7150	Approved
0.7381	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7151	Approved
0.7381	Intermediate Similarity	NPD7152	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7379	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD6881	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7356	Intermediate Similarity	NPD6932	Approved
0.7353	Intermediate Similarity	NPD4768	Approved
0.7353	Intermediate Similarity	NPD4767	Approved
0.7349	Intermediate Similarity	NPD4137	Phase 3
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.7312	Intermediate Similarity	NPD7524	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7308	Intermediate Similarity	NPD6373	Approved
0.7303	Intermediate Similarity	NPD7509	Discontinued
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD5701	Approved
0.7264	Intermediate Similarity	NPD8297	Approved
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7263	Intermediate Similarity	NPD5207	Approved
0.7262	Intermediate Similarity	NPD4789	Approved
0.7262	Intermediate Similarity	NPD4691	Approved
0.7262	Intermediate Similarity	NPD4244	Approved
0.7262	Intermediate Similarity	NPD4245	Approved
0.7253	Intermediate Similarity	NPD6695	Phase 3
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7229	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6011	Approved
0.7212	Intermediate Similarity	NPD5128	Approved
0.7212	Intermediate Similarity	NPD4730	Approved
0.7212	Intermediate Similarity	NPD4729	Approved
0.7196	Intermediate Similarity	NPD4632	Approved
0.7191	Intermediate Similarity	NPD6683	Phase 2
0.7191	Intermediate Similarity	NPD7645	Phase 2
0.7188	Intermediate Similarity	NPD6411	Approved
0.7188	Intermediate Similarity	NPD5694	Approved
0.7174	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7902	Approved
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7159	Intermediate Similarity	NPD6925	Approved
0.7159	Intermediate Similarity	NPD5776	Phase 2
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3698	Phase 2
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5275	Approved
0.7126	Intermediate Similarity	NPD4190	Phase 3
0.7111	Intermediate Similarity	NPD7514	Phase 3
0.7103	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD6893	Approved
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7145	Approved
0.7079	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5251	Approved
0.7075	Intermediate Similarity	NPD5250	Approved
0.7075	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5135	Approved
0.7075	Intermediate Similarity	NPD5248	Approved
0.7075	Intermediate Similarity	NPD5249	Phase 3
0.7075	Intermediate Similarity	NPD5169	Approved
0.7075	Intermediate Similarity	NPD5247	Approved
0.7048	Intermediate Similarity	NPD5168	Approved
0.7024	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5360	Phase 3
0.7011	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5693	Phase 1
0.701	Intermediate Similarity	NPD8035	Phase 2
0.701	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD5217	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