NPASS Compound

Structure

NPC473169 OpenBabel07101718292D 34 38 0 0 1 0 0 0 0 0999 V2000 0.4521 -2.8558 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 4.7369 -0.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7939 0.0212 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 2.0818 -2.5976 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 1.1859 -2.2147 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 2.9399 -2.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4994 -0.4872 0.0000 C 0 0 1 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 3.1138 -1.1772 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 4.0531 -0.9180 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 3.7281 -2.7086 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 4.7472 -1.6018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4728 -0.4435 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 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 16 1 6 0 0 0 20 24 1 0 0 0 0 20 34 1 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 32 2 0 0 0 0 25 27 1 6 0 0 0 25 34 1 0 0 0 0 27 33 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:	468.32
Volume:	509.269
LogP:	4.263
LogD:	3.109
LogS:	-4.327
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	5.312
Fsp3:	0.8
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:	-5.038
MDCK Permeability:	2.3342423446592875e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	92.58688354492188%
Volume Distribution (VD):	1.166
Pgp-substrate:	5.591465950012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.759
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	8.099
Half-life (T1/2):	0.641

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.449
Carcinogencity:	0.806
Eye Corrosion:	0.013
Eye Irritation:	0.027
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC473169

Natural Product ID:	NPC473169
*Common Name:**	TZUCUQTWDXYCLJ-WXECSZRISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TZUCUQTWDXYCLJ-WXECSZRISA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17-15-19(31)25(27(4,5)33)34-20-16-30(8)18(24(17)20)9-10-22-28(6)13-12-23(32)26(2,3)21(28)11-14-29(22,30)7/h9-10,17,20-22,25,33H,11-16H2,1-8H3/t17-,20+,21+,22+,25+,28+,29+,30+/m1/s1
SMILES:	CC1CC(=O)C(OC2C1=C3C=CC4C5(CCC(=O)C(C5CCC4(C3(C2)C)C)(C)C)C)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632949
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	=	58790.0	nM	PMID[504804]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	10400.0	nM	PMID[504805]

☑ 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 NPC473169 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	215
0.1-0.2	1151
0.2-0.3	4076
0.3-0.4	8763
0.4-0.5	14274
0.5-0.6	8351
0.6-0.7	5326
0.7-0.8	534
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8725	High Similarity	NPC473174
0.8476	Intermediate Similarity	NPC473175
0.8252	Intermediate Similarity	NPC473161
0.8137	Intermediate Similarity	NPC473172
0.8113	Intermediate Similarity	NPC473163
0.8037	Intermediate Similarity	NPC194323
0.7982	Intermediate Similarity	NPC144459
0.7981	Intermediate Similarity	NPC473164
0.7961	Intermediate Similarity	NPC473162
0.7909	Intermediate Similarity	NPC475418
0.7909	Intermediate Similarity	NPC473482
0.7909	Intermediate Similarity	NPC318363
0.7838	Intermediate Similarity	NPC475065
0.783	Intermediate Similarity	NPC177232
0.783	Intermediate Similarity	NPC212465
0.7818	Intermediate Similarity	NPC475294
0.7818	Intermediate Similarity	NPC329048
0.7818	Intermediate Similarity	NPC330011
0.7788	Intermediate Similarity	NPC293086
0.7778	Intermediate Similarity	NPC185530
0.7768	Intermediate Similarity	NPC29133
0.7757	Intermediate Similarity	NPC473176
0.7736	Intermediate Similarity	NPC239895
0.7731	Intermediate Similarity	NPC120724
0.7714	Intermediate Similarity	NPC280725
0.7706	Intermediate Similarity	NPC117185
0.7706	Intermediate Similarity	NPC26478
0.7699	Intermediate Similarity	NPC470961
0.7685	Intermediate Similarity	NPC323441
0.7672	Intermediate Similarity	NPC239273
0.767	Intermediate Similarity	NPC320026
0.7664	Intermediate Similarity	NPC303777
0.7664	Intermediate Similarity	NPC471582
0.7664	Intermediate Similarity	NPC471784
0.7642	Intermediate Similarity	NPC21681
0.7642	Intermediate Similarity	NPC472675
0.7642	Intermediate Similarity	NPC472733
0.7642	Intermediate Similarity	NPC472734
0.7636	Intermediate Similarity	NPC149124
0.7636	Intermediate Similarity	NPC325769
0.7636	Intermediate Similarity	NPC75531
0.7632	Intermediate Similarity	NPC100267
0.7632	Intermediate Similarity	NPC475524
0.7632	Intermediate Similarity	NPC191620
0.7624	Intermediate Similarity	NPC473168
0.7619	Intermediate Similarity	NPC477241
0.7619	Intermediate Similarity	NPC67831
0.7619	Intermediate Similarity	NPC174051
0.7615	Intermediate Similarity	NPC473928
0.7615	Intermediate Similarity	NPC87351
0.7611	Intermediate Similarity	NPC473627
0.7611	Intermediate Similarity	NPC37116
0.7607	Intermediate Similarity	NPC257457
0.7607	Intermediate Similarity	NPC311554
0.7596	Intermediate Similarity	NPC262870
0.7589	Intermediate Similarity	NPC220155
0.7573	Intermediate Similarity	NPC2983
0.757	Intermediate Similarity	NPC472073
0.757	Intermediate Similarity	NPC27105
0.757	Intermediate Similarity	NPC472732
0.757	Intermediate Similarity	NPC474977
0.757	Intermediate Similarity	NPC472731
0.757	Intermediate Similarity	NPC472074
0.7568	Intermediate Similarity	NPC173172
0.7568	Intermediate Similarity	NPC477125
0.7568	Intermediate Similarity	NPC478052
0.7568	Intermediate Similarity	NPC166607
0.7568	Intermediate Similarity	NPC60681
0.7568	Intermediate Similarity	NPC475414
0.7565	Intermediate Similarity	NPC469454
0.7565	Intermediate Similarity	NPC469496
0.7565	Intermediate Similarity	NPC469463
0.7549	Intermediate Similarity	NPC90652
0.7547	Intermediate Similarity	NPC473170
0.7547	Intermediate Similarity	NPC295347
0.7545	Intermediate Similarity	NPC329345
0.7545	Intermediate Similarity	NPC90177
0.7545	Intermediate Similarity	NPC311612
0.7545	Intermediate Similarity	NPC473283
0.7545	Intermediate Similarity	NPC475526
0.7544	Intermediate Similarity	NPC304180
0.7544	Intermediate Similarity	NPC179798
0.7542	Intermediate Similarity	NPC270850
0.7542	Intermediate Similarity	NPC305260
0.7525	Intermediate Similarity	NPC470048
0.7524	Intermediate Similarity	NPC141447
0.7523	Intermediate Similarity	NPC474327
0.7522	Intermediate Similarity	NPC214644
0.7522	Intermediate Similarity	NPC470257
0.7522	Intermediate Similarity	NPC87335
0.7521	Intermediate Similarity	NPC470493
0.7521	Intermediate Similarity	NPC312824
0.7521	Intermediate Similarity	NPC183580
0.75	Intermediate Similarity	NPC280592
0.75	Intermediate Similarity	NPC472730
0.75	Intermediate Similarity	NPC253177
0.75	Intermediate Similarity	NPC473898
0.75	Intermediate Similarity	NPC131665
0.75	Intermediate Similarity	NPC469318
0.75	Intermediate Similarity	NPC177680
0.75	Intermediate Similarity	NPC153776
0.75	Intermediate Similarity	NPC213636
0.75	Intermediate Similarity	NPC255387
0.75	Intermediate Similarity	NPC99657
0.75	Intermediate Similarity	NPC471330
0.75	Intermediate Similarity	NPC473284
0.75	Intermediate Similarity	NPC470046
0.75	Intermediate Similarity	NPC203388
0.75	Intermediate Similarity	NPC473173
0.75	Intermediate Similarity	NPC471331
0.75	Intermediate Similarity	NPC472687
0.75	Intermediate Similarity	NPC475176
0.75	Intermediate Similarity	NPC113393
0.75	Intermediate Similarity	NPC476958
0.75	Intermediate Similarity	NPC470047
0.75	Intermediate Similarity	NPC472729
0.7479	Intermediate Similarity	NPC478051
0.7478	Intermediate Similarity	NPC147180
0.7478	Intermediate Similarity	NPC264634
0.7478	Intermediate Similarity	NPC221144
0.7477	Intermediate Similarity	NPC49371
0.7477	Intermediate Similarity	NPC13385
0.7477	Intermediate Similarity	NPC137657
0.7477	Intermediate Similarity	NPC160843
0.7477	Intermediate Similarity	NPC160056
0.7477	Intermediate Similarity	NPC78473
0.7477	Intermediate Similarity	NPC472868
0.7476	Intermediate Similarity	NPC44181
0.7476	Intermediate Similarity	NPC24816
0.7476	Intermediate Similarity	NPC470417
0.7459	Intermediate Similarity	NPC181999
0.7458	Intermediate Similarity	NPC318751
0.7455	Intermediate Similarity	NPC470840
0.7455	Intermediate Similarity	NPC477915
0.7455	Intermediate Similarity	NPC80781
0.7453	Intermediate Similarity	NPC148463
0.7451	Intermediate Similarity	NPC89077
0.7451	Intermediate Similarity	NPC470050
0.7451	Intermediate Similarity	NPC470051
0.7438	Intermediate Similarity	NPC91693
0.7438	Intermediate Similarity	NPC265557
0.7438	Intermediate Similarity	NPC18945
0.7438	Intermediate Similarity	NPC105926
0.7436	Intermediate Similarity	NPC148458
0.7436	Intermediate Similarity	NPC176840
0.7436	Intermediate Similarity	NPC190286
0.7434	Intermediate Similarity	NPC177064
0.7431	Intermediate Similarity	NPC117685
0.7431	Intermediate Similarity	NPC477521
0.7431	Intermediate Similarity	NPC472727
0.7431	Intermediate Similarity	NPC54705
0.7431	Intermediate Similarity	NPC110149
0.7431	Intermediate Similarity	NPC472728
0.7429	Intermediate Similarity	NPC473167
0.7429	Intermediate Similarity	NPC248913
0.7429	Intermediate Similarity	NPC472975
0.7429	Intermediate Similarity	NPC19114
0.7429	Intermediate Similarity	NPC296114
0.7429	Intermediate Similarity	NPC471329
0.7417	Intermediate Similarity	NPC46570
0.7414	Intermediate Similarity	NPC56448
0.7411	Intermediate Similarity	NPC85529
0.7411	Intermediate Similarity	NPC32006
0.7407	Intermediate Similarity	NPC107243
0.7407	Intermediate Similarity	NPC470834
0.7407	Intermediate Similarity	NPC126815
0.7407	Intermediate Similarity	NPC208094
0.7407	Intermediate Similarity	NPC474938
0.7407	Intermediate Similarity	NPC291634
0.7407	Intermediate Similarity	NPC474785
0.7407	Intermediate Similarity	NPC57416
0.7404	Intermediate Similarity	NPC76879
0.7404	Intermediate Similarity	NPC474245
0.7404	Intermediate Similarity	NPC474570
0.7404	Intermediate Similarity	NPC469323
0.7404	Intermediate Similarity	NPC32830
0.7395	Intermediate Similarity	NPC264954
0.7391	Intermediate Similarity	NPC474315
0.7391	Intermediate Similarity	NPC474229
0.7391	Intermediate Similarity	NPC324683
0.7387	Intermediate Similarity	NPC474207
0.7387	Intermediate Similarity	NPC475050
0.7387	Intermediate Similarity	NPC111323
0.7387	Intermediate Similarity	NPC474330
0.7387	Intermediate Similarity	NPC191892
0.7387	Intermediate Similarity	NPC324001
0.7387	Intermediate Similarity	NPC72151
0.7387	Intermediate Similarity	NPC264048
0.7383	Intermediate Similarity	NPC248574
0.7383	Intermediate Similarity	NPC171395
0.7383	Intermediate Similarity	NPC209355
0.7379	Intermediate Similarity	NPC469322
0.7379	Intermediate Similarity	NPC317590
0.7377	Intermediate Similarity	NPC470922
0.7377	Intermediate Similarity	NPC476729
0.7373	Intermediate Similarity	NPC470959
0.7373	Intermediate Similarity	NPC471854
0.7373	Intermediate Similarity	NPC476959
0.7373	Intermediate Similarity	NPC470492
0.7373	Intermediate Similarity	NPC473590

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 NPC473169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1348
0.2-0.3	3669
0.3-0.4	2615
0.4-0.5	861
0.5-0.6	259
0.6-0.7	203
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7478	Intermediate Similarity	NPD8297	Approved
0.7434	Intermediate Similarity	NPD6881	Approved
0.7434	Intermediate Similarity	NPD6899	Approved
0.7411	Intermediate Similarity	NPD6402	Approved
0.7411	Intermediate Similarity	NPD5739	Approved
0.7411	Intermediate Similarity	NPD7128	Approved
0.7411	Intermediate Similarity	NPD6675	Approved
0.7407	Intermediate Similarity	NPD6084	Phase 2
0.7407	Intermediate Similarity	NPD6083	Phase 2
0.7373	Intermediate Similarity	NPD7115	Discovery
0.7345	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD6054	Approved
0.7333	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD7102	Approved
0.7304	Intermediate Similarity	NPD4634	Approved
0.7304	Intermediate Similarity	NPD7290	Approved
0.7304	Intermediate Similarity	NPD6883	Approved
0.7297	Intermediate Similarity	NPD5211	Phase 2
0.7281	Intermediate Similarity	NPD7320	Approved
0.7281	Intermediate Similarity	NPD6011	Approved
0.7273	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD4696	Approved
0.7273	Intermediate Similarity	NPD5285	Approved
0.7264	Intermediate Similarity	NPD5693	Phase 1
0.7248	Intermediate Similarity	NPD4755	Approved
0.7241	Intermediate Similarity	NPD8130	Phase 1
0.7241	Intermediate Similarity	NPD6847	Approved
0.7241	Intermediate Similarity	NPD6649	Approved
0.7241	Intermediate Similarity	NPD6617	Approved
0.7241	Intermediate Similarity	NPD6650	Approved
0.7241	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD5695	Phase 3
0.7217	Intermediate Similarity	NPD6372	Approved
0.7217	Intermediate Similarity	NPD6012	Approved
0.7217	Intermediate Similarity	NPD6013	Approved
0.7217	Intermediate Similarity	NPD6014	Approved
0.7217	Intermediate Similarity	NPD6373	Approved
0.7213	Intermediate Similarity	NPD6370	Approved
0.7207	Intermediate Similarity	NPD5223	Approved
0.7193	Intermediate Similarity	NPD5701	Approved
0.719	Intermediate Similarity	NPD6059	Approved
0.7184	Intermediate Similarity	NPD5329	Approved
0.7182	Intermediate Similarity	NPD5696	Approved
0.7179	Intermediate Similarity	NPD6882	Approved
0.7168	Intermediate Similarity	NPD5141	Approved
0.7156	Intermediate Similarity	NPD5221	Approved
0.7156	Intermediate Similarity	NPD5222	Approved
0.7156	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.7131	Intermediate Similarity	NPD6016	Approved
0.7131	Intermediate Similarity	NPD6015	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4632	Approved
0.7117	Intermediate Similarity	NPD4700	Approved
0.7115	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD6098	Approved
0.7115	Intermediate Similarity	NPD4694	Approved
0.7115	Intermediate Similarity	NPD5280	Approved
0.7103	Intermediate Similarity	NPD5694	Approved
0.7103	Intermediate Similarity	NPD6411	Approved
0.7103	Intermediate Similarity	NPD6079	Approved
0.7103	Intermediate Similarity	NPD6050	Approved
0.7097	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5173	Approved
0.7087	Intermediate Similarity	NPD3665	Phase 1
0.7087	Intermediate Similarity	NPD4786	Approved
0.7087	Intermediate Similarity	NPD3666	Approved
0.7087	Intermediate Similarity	NPD3133	Approved
0.7087	Intermediate Similarity	NPD4197	Approved
0.708	Intermediate Similarity	NPD5174	Approved
0.708	Intermediate Similarity	NPD5175	Approved
0.7075	Intermediate Similarity	NPD6904	Approved
0.7075	Intermediate Similarity	NPD6673	Approved
0.7075	Intermediate Similarity	NPD5328	Approved
0.7075	Intermediate Similarity	NPD6080	Approved
0.7073	Intermediate Similarity	NPD5988	Approved
0.7064	Intermediate Similarity	NPD4629	Approved
0.7064	Intermediate Similarity	NPD5210	Approved
0.7059	Intermediate Similarity	NPD3667	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7037	Intermediate Similarity	NPD6399	Phase 3
0.7009	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD4697	Phase 3
0.6984	Remote Similarity	NPD7078	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6952	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD4623	Approved
0.6952	Remote Similarity	NPD5690	Phase 2
0.6952	Remote Similarity	NPD4519	Discontinued
0.6952	Remote Similarity	NPD7334	Approved
0.6942	Remote Similarity	NPD6009	Approved
0.693	Remote Similarity	NPD4754	Approved
0.6929	Remote Similarity	NPD7736	Approved
0.6916	Remote Similarity	NPD6101	Approved
0.6916	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6412	Phase 2
0.6893	Remote Similarity	NPD4223	Phase 3
0.6893	Remote Similarity	NPD4221	Approved
0.6885	Remote Similarity	NPD6335	Approved
0.6881	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD5779	Approved
0.688	Remote Similarity	NPD7604	Phase 2
0.6855	Remote Similarity	NPD5983	Phase 2
0.685	Remote Similarity	NPD8293	Discontinued
0.6838	Remote Similarity	NPD4729	Approved
0.6838	Remote Similarity	NPD4730	Approved
0.6829	Remote Similarity	NPD7100	Approved
0.6829	Remote Similarity	NPD7101	Approved
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6903	Approved
0.681	Remote Similarity	NPD4767	Approved
0.681	Remote Similarity	NPD4768	Approved
0.6803	Remote Similarity	NPD6317	Approved
0.6797	Remote Similarity	NPD6033	Approved
0.6792	Remote Similarity	NPD3618	Phase 1
0.6789	Remote Similarity	NPD5284	Approved
0.6789	Remote Similarity	NPD5281	Approved
0.6772	Remote Similarity	NPD6336	Discontinued
0.6762	Remote Similarity	NPD3668	Phase 3
0.6759	Remote Similarity	NPD6051	Approved
0.6752	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6053	Discontinued
0.6748	Remote Similarity	NPD6314	Approved
0.6748	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD7319	Approved
0.6727	Remote Similarity	NPD4202	Approved
0.6726	Remote Similarity	NPD7638	Approved
0.6726	Remote Similarity	NPD4225	Approved
0.6723	Remote Similarity	NPD5249	Phase 3
0.6723	Remote Similarity	NPD5251	Approved
0.6723	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5247	Approved
0.6723	Remote Similarity	NPD5135	Approved
0.6723	Remote Similarity	NPD5250	Approved
0.6723	Remote Similarity	NPD5169	Approved
0.6723	Remote Similarity	NPD5248	Approved
0.6721	Remote Similarity	NPD6274	Approved
0.6721	Remote Similarity	NPD6868	Approved
0.6699	Remote Similarity	NPD4695	Discontinued
0.6695	Remote Similarity	NPD6686	Approved
0.6695	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6641	Remote Similarity	NPD7260	Phase 2
0.6641	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD4689	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD4138	Approved
0.6636	Remote Similarity	NPD4693	Phase 3
0.6636	Remote Similarity	NPD4688	Approved
0.6636	Remote Similarity	NPD4690	Approved
0.6636	Remote Similarity	NPD5205	Approved
0.6614	Remote Similarity	NPD8328	Phase 3
0.6607	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5654	Approved
0.6606	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6908	Approved
0.6587	Remote Similarity	NPD6909	Approved
0.6583	Remote Similarity	NPD6371	Approved
0.6577	Remote Similarity	NPD5133	Approved
0.6574	Remote Similarity	NPD7524	Approved
0.6571	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4522	Approved
0.6555	Remote Similarity	NPD5168	Approved
0.6545	Remote Similarity	NPD5207	Approved
0.6545	Remote Similarity	NPD5785	Approved
0.6518	Remote Similarity	NPD5282	Discontinued
0.6509	Remote Similarity	NPD4788	Approved
0.6504	Remote Similarity	NPD5167	Approved
0.65	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7902	Approved
0.6491	Remote Similarity	NPD5959	Approved
0.6486	Remote Similarity	NPD7983	Approved
0.6486	Remote Similarity	NPD7515	Phase 2
0.6481	Remote Similarity	NPD5786	Approved
0.6471	Remote Similarity	NPD6933	Approved
0.646	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8513	Phase 3
0.6457	Remote Similarity	NPD8515	Approved
0.6457	Remote Similarity	NPD6921	Approved
0.6457	Remote Similarity	NPD8516	Approved
0.6457	Remote Similarity	NPD7503	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