NPASS Compound

Structure

NPC473161 OpenBabel07101719132D 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 0 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 2 0 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:	484.32
Volume:	523.979
LogP:	2.993
LogD:	2.43
LogS:	-4.16
# Rotatable Bonds:	5
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	5.158
Fsp3:	0.767
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:	-5.305
MDCK Permeability:	2.7128715373692103e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.503

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917
Plasma Protein Binding (PPB):	88.6065444946289%
Volume Distribution (VD):	0.689
Pgp-substrate:	7.183046817779541%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	4.261
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.175
Carcinogencity:	0.733
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC473161

Natural Product ID:	NPC473161
*Common Name:**	GHJSMGTZWLBPHU-DSAUVPRUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GHJSMGTZWLBPHU-DSAUVPRUSA-N
Standard InCHI:	InChI=1S/C30H44O5/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/h9-10,17,21-22,25,34-35H,11-16H2,1-8H3/t17-,21+,22+,25+,28+,29+,30+/m1/s1
SMILES:	O=C([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:	CHEMBL3632941
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	=	10140.0	nM	PMID[534450]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	15470.0	nM	PMID[534451]

☑ 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 NPC473161 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	187
0.1-0.2	1041
0.2-0.3	4486
0.3-0.4	11175
0.4-0.5	12296
0.5-0.6	7180
0.6-0.7	5154
0.7-0.8	1140
0.8-0.85	33
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC473164
0.9032	High Similarity	NPC473172
0.8936	High Similarity	NPC280725
0.8632	High Similarity	NPC473162
0.8557	High Similarity	NPC472074
0.8557	High Similarity	NPC472073
0.8478	Intermediate Similarity	NPC473168
0.8421	Intermediate Similarity	NPC19114
0.84	Intermediate Similarity	NPC473163
0.8387	Intermediate Similarity	NPC90652
0.8387	Intermediate Similarity	NPC99909
0.8351	Intermediate Similarity	NPC473170
0.8333	Intermediate Similarity	NPC474807
0.8333	Intermediate Similarity	NPC233118
0.8316	Intermediate Similarity	NPC129913
0.8298	Intermediate Similarity	NPC44181
0.8298	Intermediate Similarity	NPC470417
0.8283	Intermediate Similarity	NPC147954
0.828	Intermediate Similarity	NPC89077
0.828	Intermediate Similarity	NPC327115
0.8261	Intermediate Similarity	NPC237712
0.8261	Intermediate Similarity	NPC85774
0.8261	Intermediate Similarity	NPC214043
0.8252	Intermediate Similarity	NPC473169
0.8242	Intermediate Similarity	NPC469325
0.8229	Intermediate Similarity	NPC473167
0.8211	Intermediate Similarity	NPC474245
0.8211	Intermediate Similarity	NPC32830
0.8211	Intermediate Similarity	NPC310010
0.8211	Intermediate Similarity	NPC326627
0.8191	Intermediate Similarity	NPC141292
0.8191	Intermediate Similarity	NPC58063
0.8191	Intermediate Similarity	NPC136548
0.8182	Intermediate Similarity	NPC474938
0.8182	Intermediate Similarity	NPC474785
0.8172	Intermediate Similarity	NPC79573
0.8163	Intermediate Similarity	NPC88310
0.8152	Intermediate Similarity	NPC86370
0.8144	Intermediate Similarity	NPC474736
0.8137	Intermediate Similarity	NPC239716
0.8137	Intermediate Similarity	NPC475050
0.8132	Intermediate Similarity	NPC121984
0.8119	Intermediate Similarity	NPC473174
0.8105	Intermediate Similarity	NPC310752
0.8105	Intermediate Similarity	NPC292491
0.8085	Intermediate Similarity	NPC31564
0.8085	Intermediate Similarity	NPC51014
0.8085	Intermediate Similarity	NPC474778
0.8085	Intermediate Similarity	NPC474733
0.8085	Intermediate Similarity	NPC145879
0.8085	Intermediate Similarity	NPC194417
0.8085	Intermediate Similarity	NPC474732
0.8085	Intermediate Similarity	NPC94666
0.8081	Intermediate Similarity	NPC471153
0.8065	Intermediate Similarity	NPC473246
0.8065	Intermediate Similarity	NPC321187
0.8065	Intermediate Similarity	NPC329043
0.8065	Intermediate Similarity	NPC58841
0.8065	Intermediate Similarity	NPC161423
0.8065	Intermediate Similarity	NPC227064
0.8061	Intermediate Similarity	NPC299100
0.8061	Intermediate Similarity	NPC196485
0.8061	Intermediate Similarity	NPC8993
0.8061	Intermediate Similarity	NPC245972
0.8043	Intermediate Similarity	NPC212083
0.8041	Intermediate Similarity	NPC475806
0.8041	Intermediate Similarity	NPC168027
0.8041	Intermediate Similarity	NPC185936
0.8022	Intermediate Similarity	NPC2482
0.8021	Intermediate Similarity	NPC31985
0.8021	Intermediate Similarity	NPC477943
0.8021	Intermediate Similarity	NPC76879
0.8021	Intermediate Similarity	NPC1015
0.802	Intermediate Similarity	NPC110149
0.8	Intermediate Similarity	NPC96496
0.8	Intermediate Similarity	NPC475740
0.8	Intermediate Similarity	NPC93778
0.7981	Intermediate Similarity	NPC166607
0.798	Intermediate Similarity	NPC180950
0.7979	Intermediate Similarity	NPC470574
0.7979	Intermediate Similarity	NPC469948
0.7961	Intermediate Similarity	NPC117185
0.7959	Intermediate Similarity	NPC211230
0.7959	Intermediate Similarity	NPC134826
0.7941	Intermediate Similarity	NPC282524
0.7938	Intermediate Similarity	NPC320026
0.7938	Intermediate Similarity	NPC85173
0.7935	Intermediate Similarity	NPC116797
0.7935	Intermediate Similarity	NPC14151
0.7921	Intermediate Similarity	NPC191565
0.7921	Intermediate Similarity	NPC153776
0.7921	Intermediate Similarity	NPC472729
0.7921	Intermediate Similarity	NPC472730
0.7921	Intermediate Similarity	NPC177680
0.7917	Intermediate Similarity	NPC328313
0.7912	Intermediate Similarity	NPC474113
0.7905	Intermediate Similarity	NPC58370
0.7905	Intermediate Similarity	NPC330011
0.7905	Intermediate Similarity	NPC43285
0.7905	Intermediate Similarity	NPC473284
0.7905	Intermediate Similarity	NPC329048
0.7905	Intermediate Similarity	NPC185
0.79	Intermediate Similarity	NPC269492
0.79	Intermediate Similarity	NPC21681
0.79	Intermediate Similarity	NPC472675
0.7895	Intermediate Similarity	NPC229717
0.7895	Intermediate Similarity	NPC118648
0.7895	Intermediate Similarity	NPC222613
0.7895	Intermediate Similarity	NPC475022
0.7895	Intermediate Similarity	NPC158393
0.7895	Intermediate Similarity	NPC20688
0.7889	Intermediate Similarity	NPC325946
0.7885	Intermediate Similarity	NPC160843
0.7879	Intermediate Similarity	NPC67831
0.7879	Intermediate Similarity	NPC49670
0.7879	Intermediate Similarity	NPC474328
0.7879	Intermediate Similarity	NPC318332
0.7879	Intermediate Similarity	NPC474690
0.7879	Intermediate Similarity	NPC474882
0.7879	Intermediate Similarity	NPC174051
0.7872	Intermediate Similarity	NPC82902
0.7872	Intermediate Similarity	NPC221758
0.7872	Intermediate Similarity	NPC144258
0.7872	Intermediate Similarity	NPC473157
0.7872	Intermediate Similarity	NPC59453
0.7864	Intermediate Similarity	NPC87351
0.7857	Intermediate Similarity	NPC155304
0.7857	Intermediate Similarity	NPC262870
0.7857	Intermediate Similarity	NPC272746
0.7857	Intermediate Similarity	NPC473998
0.785	Intermediate Similarity	NPC235077
0.7849	Intermediate Similarity	NPC48362
0.7849	Intermediate Similarity	NPC151519
0.7849	Intermediate Similarity	NPC103486
0.7843	Intermediate Similarity	NPC472727
0.7843	Intermediate Similarity	NPC144956
0.7843	Intermediate Similarity	NPC472728
0.7835	Intermediate Similarity	NPC186688
0.7835	Intermediate Similarity	NPC26959
0.7835	Intermediate Similarity	NPC229871
0.7835	Intermediate Similarity	NPC119416
0.7835	Intermediate Similarity	NPC469319
0.7835	Intermediate Similarity	NPC2983
0.7835	Intermediate Similarity	NPC268406
0.7835	Intermediate Similarity	NPC184663
0.7835	Intermediate Similarity	NPC309603
0.7835	Intermediate Similarity	NPC473999
0.7822	Intermediate Similarity	NPC43747
0.7822	Intermediate Similarity	NPC273269
0.7822	Intermediate Similarity	NPC18509
0.7812	Intermediate Similarity	NPC469314
0.7812	Intermediate Similarity	NPC241875
0.7812	Intermediate Similarity	NPC317590
0.7812	Intermediate Similarity	NPC287079
0.7812	Intermediate Similarity	NPC469317
0.78	Intermediate Similarity	NPC139459
0.78	Intermediate Similarity	NPC263347
0.7789	Intermediate Similarity	NPC474218
0.7789	Intermediate Similarity	NPC471224
0.7788	Intermediate Similarity	NPC247957
0.7788	Intermediate Similarity	NPC320294
0.7788	Intermediate Similarity	NPC249187
0.7788	Intermediate Similarity	NPC311612
0.7778	Intermediate Similarity	NPC109305
0.7778	Intermediate Similarity	NPC12722
0.7778	Intermediate Similarity	NPC475255
0.7778	Intermediate Similarity	NPC250575
0.7757	Intermediate Similarity	NPC214644
0.7757	Intermediate Similarity	NPC470257
0.7757	Intermediate Similarity	NPC475065
0.7755	Intermediate Similarity	NPC48010
0.7755	Intermediate Similarity	NPC126993
0.7755	Intermediate Similarity	NPC171441
0.7745	Intermediate Similarity	NPC471717
0.7745	Intermediate Similarity	NPC471582
0.7745	Intermediate Similarity	NPC103051
0.7742	Intermediate Similarity	NPC189237
0.7742	Intermediate Similarity	NPC225515
0.7736	Intermediate Similarity	NPC165873
0.7732	Intermediate Similarity	NPC328539
0.7732	Intermediate Similarity	NPC474854
0.7732	Intermediate Similarity	NPC53911
0.7732	Intermediate Similarity	NPC158778
0.7732	Intermediate Similarity	NPC471722
0.7732	Intermediate Similarity	NPC471724
0.7723	Intermediate Similarity	NPC472941
0.7723	Intermediate Similarity	NPC301534
0.7723	Intermediate Similarity	NPC250757
0.7723	Intermediate Similarity	NPC249954
0.7723	Intermediate Similarity	NPC456
0.7723	Intermediate Similarity	NPC471463
0.7723	Intermediate Similarity	NPC472733
0.7723	Intermediate Similarity	NPC192428
0.7723	Intermediate Similarity	NPC49371
0.7723	Intermediate Similarity	NPC117133
0.7723	Intermediate Similarity	NPC472734
0.7723	Intermediate Similarity	NPC473158
0.7714	Intermediate Similarity	NPC473175
0.7708	Intermediate Similarity	NPC72133
0.7708	Intermediate Similarity	NPC324063

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 NPC473161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1297
0.2-0.3	3800
0.3-0.4	2622
0.4-0.5	803
0.5-0.6	191
0.6-0.7	147
0.7-0.8	118
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD5210	Approved
0.8351	Intermediate Similarity	NPD4629	Approved
0.828	Intermediate Similarity	NPD5279	Phase 3
0.8211	Intermediate Similarity	NPD4753	Phase 2
0.8065	Intermediate Similarity	NPD3133	Approved
0.8065	Intermediate Similarity	NPD3665	Phase 1
0.8065	Intermediate Similarity	NPD3666	Approved
0.7979	Intermediate Similarity	NPD5329	Approved
0.79	Intermediate Similarity	NPD5222	Approved
0.79	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD5280	Approved
0.7895	Intermediate Similarity	NPD3618	Phase 1
0.7895	Intermediate Similarity	NPD4694	Approved
0.7872	Intermediate Similarity	NPD4786	Approved
0.7872	Intermediate Similarity	NPD4197	Approved
0.7857	Intermediate Similarity	NPD6079	Approved
0.785	Intermediate Similarity	NPD4634	Approved
0.7849	Intermediate Similarity	NPD3667	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7835	Intermediate Similarity	NPD5328	Approved
0.7822	Intermediate Similarity	NPD6083	Phase 2
0.7822	Intermediate Similarity	NPD5173	Approved
0.7822	Intermediate Similarity	NPD6084	Phase 2
0.7822	Intermediate Similarity	NPD4755	Approved
0.7767	Intermediate Similarity	NPD5223	Approved
0.7745	Intermediate Similarity	NPD5696	Approved
0.7723	Intermediate Similarity	NPD4697	Phase 3
0.7708	Intermediate Similarity	NPD5690	Phase 2
0.7708	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD5226	Approved
0.767	Intermediate Similarity	NPD4700	Approved
0.766	Intermediate Similarity	NPD4223	Phase 3
0.766	Intermediate Similarity	NPD4221	Approved
0.7634	Intermediate Similarity	NPD4695	Discontinued
0.7619	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7609	Intermediate Similarity	NPD3617	Approved
0.76	Intermediate Similarity	NPD4202	Approved
0.7551	Intermediate Similarity	NPD6672	Approved
0.7551	Intermediate Similarity	NPD5737	Approved
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD4623	Approved
0.7526	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7475	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4754	Approved
0.7451	Intermediate Similarity	NPD5695	Phase 3
0.7407	Intermediate Similarity	NPD5697	Approved
0.7387	Intermediate Similarity	NPD8297	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD5091	Approved
0.7347	Intermediate Similarity	NPD5205	Approved
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD4693	Phase 3
0.7347	Intermediate Similarity	NPD4138	Approved
0.7347	Intermediate Similarity	NPD4689	Approved
0.7347	Intermediate Similarity	NPD4688	Approved
0.7347	Intermediate Similarity	NPD4690	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD6011	Approved
0.7339	Intermediate Similarity	NPD7320	Approved
0.7327	Intermediate Similarity	NPD6050	Approved
0.7327	Intermediate Similarity	NPD5694	Approved
0.7321	Intermediate Similarity	NPD4632	Approved
0.732	Intermediate Similarity	NPD3668	Phase 3
0.7315	Intermediate Similarity	NPD4768	Approved
0.7315	Intermediate Similarity	NPD4767	Approved
0.7304	Intermediate Similarity	NPD4522	Approved
0.73	Intermediate Similarity	NPD6904	Approved
0.73	Intermediate Similarity	NPD6080	Approved
0.73	Intermediate Similarity	NPD6673	Approved
0.7297	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD8130	Phase 1
0.7297	Intermediate Similarity	NPD6847	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7297	Intermediate Similarity	NPD6650	Approved
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7263	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7255	Intermediate Similarity	NPD5133	Approved
0.7248	Intermediate Similarity	NPD5701	Approved
0.7248	Intermediate Similarity	NPD6412	Phase 2
0.7241	Intermediate Similarity	NPD6054	Approved
0.7241	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7228	Intermediate Similarity	NPD5692	Phase 3
0.7216	Intermediate Similarity	NPD4788	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.7204	Intermediate Similarity	NPD6933	Approved
0.72	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7748	Approved
0.7182	Intermediate Similarity	NPD5168	Approved
0.7182	Intermediate Similarity	NPD5128	Approved
0.7174	Intermediate Similarity	NPD4058	Approved
0.7158	Intermediate Similarity	NPD4195	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7119	Intermediate Similarity	NPD6370	Approved
0.7094	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD4096	Approved
0.7034	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD6015	Approved
0.703	Intermediate Similarity	NPD4518	Approved
0.7019	Intermediate Similarity	NPD5282	Discontinued
0.7	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.699	Remote Similarity	NPD5693	Phase 1
0.6989	Remote Similarity	NPD4687	Approved
0.6989	Remote Similarity	NPD6924	Approved
0.6989	Remote Similarity	NPD6926	Approved
0.6989	Remote Similarity	NPD5733	Approved
0.6983	Remote Similarity	NPD6009	Approved
0.6981	Remote Similarity	NPD7902	Approved
0.6975	Remote Similarity	NPD5988	Approved
0.6961	Remote Similarity	NPD6101	Approved
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5167	Approved
0.6942	Remote Similarity	NPD6616	Approved
0.6923	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD4137	Phase 3
0.6915	Remote Similarity	NPD6942	Approved
0.6915	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD7525	Registered
0.69	Remote Similarity	NPD1696	Phase 3
0.6897	Remote Similarity	NPD6868	Approved
0.6893	Remote Similarity	NPD5207	Approved
0.6885	Remote Similarity	NPD7078	Approved
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.6848	Remote Similarity	NPD4747	Approved
0.6848	Remote Similarity	NPD4691	Approved
0.6842	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6317	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6792	Remote Similarity	NPD5654	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6614	Approved
0.678	Remote Similarity	NPD6314	Approved
0.678	Remote Similarity	NPD6313	Approved
0.6777	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD5276	Approved
0.6759	Remote Similarity	NPD7638	Approved
0.6752	Remote Similarity	NPD6274	Approved
0.675	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD8293	Discontinued
0.6735	Remote Similarity	NPD7509	Discontinued
0.6733	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7614	Phase 1
0.6701	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5208	Approved
0.6698	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7900	Approved
0.6697	Remote Similarity	NPD7640	Approved
0.6697	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD4139	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