NPASS Compound

Structure

CID147954 OpenBabel06191715522D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.0805 -1.7514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3563 3.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 3.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5474 0.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 2.9050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8396 2.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3555 0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5175 2.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5173 1.4517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1940 1.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8394 1.4522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6779 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 -0.4841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1943 2.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3560 2.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9681 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6782 0.9676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5592 -2.0989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0597 0.9507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5430 -0.4990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5438 -0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0605 2.9196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 25 2 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 24 1 6 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 27 1 1 0 0 0 17 22 1 1 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 18 28 2 0 0 0 0 19 23 1 6 0 0 0 20 21 1 0 0 0 0 20 29 2 0 0 0 0 22 23 1 1 0 0 0 23 5 1 6 0 0 0 24 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	420.203
LogP:	2.13
LogD:	1.888
LogS:	-4.156
# Rotatable Bonds:	1
TPSA:	88.51
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	5.257
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021
MDCK Permeability:	4.283184534870088e-05
Pgp-inhibitor:	0.876
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	70.95881652832031%
Volume Distribution (VD):	0.399
Pgp-substrate:	29.455846786499023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.632

ADMET: Excretion

Clearance (CL):	16.243
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.466
Skin Sensitization:	0.35
Carcinogencity:	0.672
Eye Corrosion:	0.039
Eye Irritation:	0.025
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC147954

Natural Product ID:	NPC147954
*Common Name:**	(8S,9R,10R,13R,14S,16R,17R)-17-Acetyl-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-8,10,12,15,16,17-Hexahydro-7H-Cyclopenta[A]Phenanthrene-3,11-Dione
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-acetyl-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:
Standard InCHIKey:	YDJNVIWFYBBVAK-XDISOHHISA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-12(25)19-16(27)10-22(4)17-8-7-13-14(9-15(26)20(29)21(13,2)3)24(17,6)18(28)11-23(19,22)5/h7,9,14,16-17,19,26-27H,8,10-11H2,1-6H3/t14-,16-,17+,19+,22+,23-,24+/m1/s1
SMILES:	CC(=O)[C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(C(=O)C4(C)C)O)[C@]3(C)C(=O)C[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017892
PubChem CID:	70681229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003058] 20-oxosteroids

*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
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[555294]

☑ 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 NPC147954 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	179
0.1-0.2	1320
0.2-0.3	5979
0.3-0.4	12650
0.4-0.5	9794
0.5-0.6	7244
0.6-0.7	4283
0.7-0.8	1086
0.8-0.85	143
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC474720
0.89	High Similarity	NPC43285
0.89	High Similarity	NPC58370
0.8788	High Similarity	NPC111323
0.8725	High Similarity	NPC470257
0.871	High Similarity	NPC477943
0.866	High Similarity	NPC43747
0.8646	High Similarity	NPC472932
0.8632	High Similarity	NPC233118
0.8587	High Similarity	NPC327115
0.8571	High Similarity	NPC473246
0.8571	High Similarity	NPC197386
0.8529	High Similarity	NPC185
0.8526	High Similarity	NPC168027
0.8526	High Similarity	NPC185936
0.8511	High Similarity	NPC275740
0.8511	High Similarity	NPC86319
0.8511	High Similarity	NPC326627
0.8511	High Similarity	NPC310010
0.85	High Similarity	NPC87351
0.8485	Intermediate Similarity	NPC110149
0.8485	Intermediate Similarity	NPC287833
0.8485	Intermediate Similarity	NPC144956
0.8469	Intermediate Similarity	NPC18509
0.8454	Intermediate Similarity	NPC241156
0.8438	Intermediate Similarity	NPC472930
0.8438	Intermediate Similarity	NPC474807
0.8438	Intermediate Similarity	NPC250575
0.8421	Intermediate Similarity	NPC129913
0.8416	Intermediate Similarity	NPC311612
0.8404	Intermediate Similarity	NPC471724
0.8404	Intermediate Similarity	NPC143767
0.8404	Intermediate Similarity	NPC131470
0.8404	Intermediate Similarity	NPC328313
0.84	Intermediate Similarity	NPC472924
0.8381	Intermediate Similarity	NPC472928
0.837	Intermediate Similarity	NPC58841
0.837	Intermediate Similarity	NPC214043
0.837	Intermediate Similarity	NPC82902
0.837	Intermediate Similarity	NPC237712
0.837	Intermediate Similarity	NPC227064
0.837	Intermediate Similarity	NPC321187
0.837	Intermediate Similarity	NPC161423
0.837	Intermediate Similarity	NPC85774
0.837	Intermediate Similarity	NPC329043
0.8367	Intermediate Similarity	NPC96859
0.8367	Intermediate Similarity	NPC125622
0.8367	Intermediate Similarity	NPC49371
0.8367	Intermediate Similarity	NPC472941
0.8367	Intermediate Similarity	NPC305483
0.8367	Intermediate Similarity	NPC456
0.8367	Intermediate Similarity	NPC328162
0.8365	Intermediate Similarity	NPC304495
0.8352	Intermediate Similarity	NPC103486
0.835	Intermediate Similarity	NPC472925
0.8333	Intermediate Similarity	NPC235889
0.8317	Intermediate Similarity	NPC163249
0.8317	Intermediate Similarity	NPC473424
0.8316	Intermediate Similarity	NPC76879
0.8316	Intermediate Similarity	NPC123912
0.83	Intermediate Similarity	NPC51370
0.8298	Intermediate Similarity	NPC99909
0.8298	Intermediate Similarity	NPC317590
0.8283	Intermediate Similarity	NPC273269
0.8283	Intermediate Similarity	NPC473161
0.8283	Intermediate Similarity	NPC472690
0.8283	Intermediate Similarity	NPC472689
0.8283	Intermediate Similarity	NPC477268
0.8283	Intermediate Similarity	NPC477267
0.828	Intermediate Similarity	NPC469948
0.828	Intermediate Similarity	NPC474218
0.8269	Intermediate Similarity	NPC295244
0.8265	Intermediate Similarity	NPC263347
0.8252	Intermediate Similarity	NPC181265
0.8247	Intermediate Similarity	NPC25750
0.8247	Intermediate Similarity	NPC69454
0.8247	Intermediate Similarity	NPC206810
0.8242	Intermediate Similarity	NPC116797
0.8235	Intermediate Similarity	NPC117185
0.8229	Intermediate Similarity	NPC183283
0.8229	Intermediate Similarity	NPC191684
0.8224	Intermediate Similarity	NPC472929
0.8211	Intermediate Similarity	NPC53911
0.8211	Intermediate Similarity	NPC474854
0.8211	Intermediate Similarity	NPC328539
0.8211	Intermediate Similarity	NPC471722
0.82	Intermediate Similarity	NPC235464
0.82	Intermediate Similarity	NPC166745
0.8191	Intermediate Similarity	NPC20688
0.8191	Intermediate Similarity	NPC222613
0.8191	Intermediate Similarity	NPC474778
0.8191	Intermediate Similarity	NPC118648
0.8191	Intermediate Similarity	NPC229717
0.8191	Intermediate Similarity	NPC475022
0.8191	Intermediate Similarity	NPC474732
0.8191	Intermediate Similarity	NPC51014
0.8191	Intermediate Similarity	NPC72133
0.8191	Intermediate Similarity	NPC31564
0.8191	Intermediate Similarity	NPC469994
0.8191	Intermediate Similarity	NPC474733
0.8191	Intermediate Similarity	NPC145879
0.819	Intermediate Similarity	NPC470615
0.8182	Intermediate Similarity	NPC249954
0.8182	Intermediate Similarity	NPC192428
0.8172	Intermediate Similarity	NPC144258
0.8163	Intermediate Similarity	NPC111015
0.8163	Intermediate Similarity	NPC245972
0.8163	Intermediate Similarity	NPC166906
0.8163	Intermediate Similarity	NPC196485
0.8155	Intermediate Similarity	NPC137657
0.8144	Intermediate Similarity	NPC63748
0.8144	Intermediate Similarity	NPC19114
0.8137	Intermediate Similarity	NPC204450
0.8137	Intermediate Similarity	NPC195290
0.8131	Intermediate Similarity	NPC221144
0.8125	Intermediate Similarity	NPC31985
0.8125	Intermediate Similarity	NPC1015
0.8125	Intermediate Similarity	NPC474245
0.8125	Intermediate Similarity	NPC186688
0.8125	Intermediate Similarity	NPC216866
0.8125	Intermediate Similarity	NPC54689
0.8119	Intermediate Similarity	NPC88198
0.8119	Intermediate Similarity	NPC15390
0.8119	Intermediate Similarity	NPC157787
0.8113	Intermediate Similarity	NPC235077
0.8105	Intermediate Similarity	NPC475740
0.8105	Intermediate Similarity	NPC93778
0.8105	Intermediate Similarity	NPC136548
0.8105	Intermediate Similarity	NPC96496
0.8105	Intermediate Similarity	NPC58063
0.81	Intermediate Similarity	NPC472073
0.81	Intermediate Similarity	NPC472074
0.8085	Intermediate Similarity	NPC36350
0.8085	Intermediate Similarity	NPC474083
0.8081	Intermediate Similarity	NPC173875
0.8081	Intermediate Similarity	NPC259286
0.8081	Intermediate Similarity	NPC470016
0.8081	Intermediate Similarity	NPC174948
0.8081	Intermediate Similarity	NPC280725
0.8081	Intermediate Similarity	NPC469995
0.8081	Intermediate Similarity	NPC255809
0.8081	Intermediate Similarity	NPC318282
0.8081	Intermediate Similarity	NPC37646
0.8081	Intermediate Similarity	NPC317586
0.8065	Intermediate Similarity	NPC476082
0.8065	Intermediate Similarity	NPC62214
0.8065	Intermediate Similarity	NPC278648
0.8061	Intermediate Similarity	NPC472942
0.8061	Intermediate Similarity	NPC152897
0.8061	Intermediate Similarity	NPC66429
0.8058	Intermediate Similarity	NPC236390
0.8043	Intermediate Similarity	NPC55869
0.8043	Intermediate Similarity	NPC189237
0.8041	Intermediate Similarity	NPC320026
0.8041	Intermediate Similarity	NPC69622
0.8041	Intermediate Similarity	NPC171441
0.8039	Intermediate Similarity	NPC163372
0.8039	Intermediate Similarity	NPC302537
0.8022	Intermediate Similarity	NPC472490
0.8019	Intermediate Similarity	NPC241927
0.8019	Intermediate Similarity	NPC214644
0.8019	Intermediate Similarity	NPC258543
0.8	Intermediate Similarity	NPC472934
0.8	Intermediate Similarity	NPC243525
0.8	Intermediate Similarity	NPC473164
0.8	Intermediate Similarity	NPC173272
0.8	Intermediate Similarity	NPC3772
0.8	Intermediate Similarity	NPC95565
0.8	Intermediate Similarity	NPC40765
0.8	Intermediate Similarity	NPC472927
0.8	Intermediate Similarity	NPC328371
0.8	Intermediate Similarity	NPC165873
0.8	Intermediate Similarity	NPC44063
0.7981	Intermediate Similarity	NPC13385
0.798	Intermediate Similarity	NPC23170
0.7979	Intermediate Similarity	NPC221758
0.7979	Intermediate Similarity	NPC472265
0.7979	Intermediate Similarity	NPC59453
0.7961	Intermediate Similarity	NPC119601
0.7961	Intermediate Similarity	NPC477915
0.7961	Intermediate Similarity	NPC308726
0.7961	Intermediate Similarity	NPC293753
0.7959	Intermediate Similarity	NPC154101
0.7959	Intermediate Similarity	NPC272746
0.7959	Intermediate Similarity	NPC473998
0.7959	Intermediate Similarity	NPC99380
0.7957	Intermediate Similarity	NPC193347
0.7938	Intermediate Similarity	NPC472970
0.7938	Intermediate Similarity	NPC26959
0.7938	Intermediate Similarity	NPC472971
0.7938	Intermediate Similarity	NPC268406
0.7938	Intermediate Similarity	NPC473999
0.7938	Intermediate Similarity	NPC309603
0.7938	Intermediate Similarity	NPC2983
0.7938	Intermediate Similarity	NPC184663
0.7935	Intermediate Similarity	NPC108955
0.7935	Intermediate Similarity	NPC472478
0.7921	Intermediate Similarity	NPC106557
0.7921	Intermediate Similarity	NPC18319
0.7921	Intermediate Similarity	NPC121339

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 NPC147954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1683
0.2-0.3	4230
0.3-0.4	2152
0.4-0.5	484
0.5-0.6	173
0.6-0.7	116
0.7-0.8	122
0.8-0.85	33
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8646	High Similarity	NPD5210	Approved
0.8646	High Similarity	NPD4629	Approved
0.8511	High Similarity	NPD4753	Phase 2
0.8485	Intermediate Similarity	NPD4696	Approved
0.8485	Intermediate Similarity	NPD5285	Approved
0.8485	Intermediate Similarity	NPD5286	Approved
0.8469	Intermediate Similarity	NPD4755	Approved
0.84	Intermediate Similarity	NPD5223	Approved
0.8387	Intermediate Similarity	NPD5279	Phase 3
0.8387	Intermediate Similarity	NPD5690	Phase 2
0.837	Intermediate Similarity	NPD3133	Approved
0.837	Intermediate Similarity	NPD3666	Approved
0.837	Intermediate Similarity	NPD3665	Phase 1
0.8367	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD5222	Approved
0.8367	Intermediate Similarity	NPD5221	Approved
0.8333	Intermediate Similarity	NPD6079	Approved
0.8317	Intermediate Similarity	NPD4633	Approved
0.8317	Intermediate Similarity	NPD5225	Approved
0.8317	Intermediate Similarity	NPD5224	Approved
0.8317	Intermediate Similarity	NPD5226	Approved
0.8317	Intermediate Similarity	NPD5211	Phase 2
0.8316	Intermediate Similarity	NPD5328	Approved
0.83	Intermediate Similarity	NPD4700	Approved
0.8283	Intermediate Similarity	NPD5173	Approved
0.828	Intermediate Similarity	NPD5329	Approved
0.8235	Intermediate Similarity	NPD5174	Approved
0.8235	Intermediate Similarity	NPD5175	Approved
0.8191	Intermediate Similarity	NPD4694	Approved
0.8191	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4697	Phase 3
0.8172	Intermediate Similarity	NPD4197	Approved
0.8155	Intermediate Similarity	NPD5141	Approved
0.8113	Intermediate Similarity	NPD4634	Approved
0.81	Intermediate Similarity	NPD6084	Phase 2
0.81	Intermediate Similarity	NPD6083	Phase 2
0.8095	Intermediate Similarity	NPD6899	Approved
0.8095	Intermediate Similarity	NPD6881	Approved
0.8081	Intermediate Similarity	NPD5695	Phase 3
0.8077	Intermediate Similarity	NPD7128	Approved
0.8077	Intermediate Similarity	NPD6675	Approved
0.8077	Intermediate Similarity	NPD6402	Approved
0.8077	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD4754	Approved
0.802	Intermediate Similarity	NPD5696	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7979	Intermediate Similarity	NPD4786	Approved
0.7957	Intermediate Similarity	NPD4223	Phase 3
0.7957	Intermediate Similarity	NPD4221	Approved
0.7944	Intermediate Similarity	NPD7290	Approved
0.7944	Intermediate Similarity	NPD7102	Approved
0.7944	Intermediate Similarity	NPD6883	Approved
0.7925	Intermediate Similarity	NPD5128	Approved
0.7925	Intermediate Similarity	NPD4730	Approved
0.7925	Intermediate Similarity	NPD7320	Approved
0.7925	Intermediate Similarity	NPD6011	Approved
0.7925	Intermediate Similarity	NPD4729	Approved
0.7905	Intermediate Similarity	NPD4768	Approved
0.7905	Intermediate Similarity	NPD4767	Approved
0.7879	Intermediate Similarity	NPD4202	Approved
0.7872	Intermediate Similarity	NPD4788	Approved
0.787	Intermediate Similarity	NPD6650	Approved
0.787	Intermediate Similarity	NPD6617	Approved
0.787	Intermediate Similarity	NPD6649	Approved
0.787	Intermediate Similarity	NPD6869	Approved
0.787	Intermediate Similarity	NPD8130	Phase 1
0.787	Intermediate Similarity	NPD6847	Approved
0.785	Intermediate Similarity	NPD6013	Approved
0.785	Intermediate Similarity	NPD6012	Approved
0.785	Intermediate Similarity	NPD6373	Approved
0.785	Intermediate Similarity	NPD6372	Approved
0.785	Intermediate Similarity	NPD6014	Approved
0.783	Intermediate Similarity	NPD5701	Approved
0.7812	Intermediate Similarity	NPD3618	Phase 1
0.7812	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD8297	Approved
0.7798	Intermediate Similarity	NPD6882	Approved
0.7778	Intermediate Similarity	NPD5250	Approved
0.7778	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5247	Approved
0.7778	Intermediate Similarity	NPD5248	Approved
0.7778	Intermediate Similarity	NPD5249	Phase 3
0.7778	Intermediate Similarity	NPD5135	Approved
0.7778	Intermediate Similarity	NPD5169	Approved
0.7778	Intermediate Similarity	NPD5251	Approved
0.7766	Intermediate Similarity	NPD3667	Approved
0.7742	Intermediate Similarity	NPD4695	Discontinued
0.7717	Intermediate Similarity	NPD3617	Approved
0.7706	Intermediate Similarity	NPD5127	Approved
0.7706	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5217	Approved
0.7706	Intermediate Similarity	NPD5215	Approved
0.7706	Intermediate Similarity	NPD5216	Approved
0.7653	Intermediate Similarity	NPD5737	Approved
0.7653	Intermediate Similarity	NPD6672	Approved
0.7632	Intermediate Similarity	NPD6054	Approved
0.7629	Intermediate Similarity	NPD5205	Approved
0.7629	Intermediate Similarity	NPD7334	Approved
0.7629	Intermediate Similarity	NPD7521	Approved
0.7629	Intermediate Similarity	NPD5330	Approved
0.7629	Intermediate Similarity	NPD7146	Approved
0.7629	Intermediate Similarity	NPD6409	Approved
0.7629	Intermediate Similarity	NPD4689	Approved
0.7629	Intermediate Similarity	NPD4688	Approved
0.7629	Intermediate Similarity	NPD6684	Approved
0.7629	Intermediate Similarity	NPD4138	Approved
0.7629	Intermediate Similarity	NPD4693	Phase 3
0.7629	Intermediate Similarity	NPD4690	Approved
0.7619	Intermediate Similarity	NPD5091	Approved
0.76	Intermediate Similarity	NPD5281	Approved
0.76	Intermediate Similarity	NPD6050	Approved
0.76	Intermediate Similarity	NPD5284	Approved
0.7593	Intermediate Similarity	NPD5168	Approved
0.7576	Intermediate Similarity	NPD6673	Approved
0.7576	Intermediate Similarity	NPD6080	Approved
0.7576	Intermediate Similarity	NPD6904	Approved
0.7568	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD5133	Approved
0.75	Intermediate Similarity	NPD5692	Phase 3
0.75	Intermediate Similarity	NPD5167	Approved
0.75	Intermediate Similarity	NPD6370	Approved
0.7478	Intermediate Similarity	NPD6059	Approved
0.7478	Intermediate Similarity	NPD6319	Approved
0.7475	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6903	Approved
0.7456	Intermediate Similarity	NPD6335	Approved
0.7447	Intermediate Similarity	NPD4195	Approved
0.7434	Intermediate Similarity	NPD6274	Approved
0.7426	Intermediate Similarity	NPD5694	Approved
0.7414	Intermediate Similarity	NPD6015	Approved
0.7414	Intermediate Similarity	NPD6016	Approved
0.7391	Intermediate Similarity	NPD7101	Approved
0.7391	Intermediate Similarity	NPD7100	Approved
0.7373	Intermediate Similarity	NPD7492	Approved
0.7368	Intermediate Similarity	NPD6317	Approved
0.7368	Intermediate Similarity	NPD6009	Approved
0.7353	Intermediate Similarity	NPD6399	Phase 3
0.735	Intermediate Similarity	NPD5988	Approved
0.7327	Intermediate Similarity	NPD4096	Approved
0.7311	Intermediate Similarity	NPD6616	Approved
0.7304	Intermediate Similarity	NPD6313	Approved
0.7304	Intermediate Similarity	NPD6314	Approved
0.7292	Intermediate Similarity	NPD4139	Approved
0.7292	Intermediate Similarity	NPD4692	Approved
0.7281	Intermediate Similarity	NPD6868	Approved
0.7273	Intermediate Similarity	NPD6098	Approved
0.7255	Intermediate Similarity	NPD7515	Phase 2
0.7255	Intermediate Similarity	NPD5693	Phase 1
0.725	Intermediate Similarity	NPD7078	Approved
0.7245	Intermediate Similarity	NPD3668	Phase 3
0.7241	Intermediate Similarity	NPD4522	Approved
0.7228	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7736	Approved
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7129	Intermediate Similarity	NPD4518	Approved
0.7128	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6908	Approved
0.7119	Intermediate Similarity	NPD6909	Approved
0.7119	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD8293	Discontinued
0.7097	Intermediate Similarity	NPD5733	Approved
0.7087	Intermediate Similarity	NPD6411	Approved
0.7049	Intermediate Similarity	NPD6033	Approved
0.7048	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5654	Approved
0.7027	Intermediate Similarity	NPD6614	Approved
0.7025	Intermediate Similarity	NPD6336	Discontinued
0.7021	Intermediate Similarity	NPD7339	Approved
0.7021	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD5363	Approved
0.699	Remote Similarity	NPD5785	Approved
0.699	Remote Similarity	NPD5207	Approved
0.6981	Remote Similarity	NPD7614	Phase 1
0.6961	Remote Similarity	NPD5208	Approved
0.6957	Remote Similarity	NPD4691	Approved
0.6957	Remote Similarity	NPD4747	Approved
0.6952	Remote Similarity	NPD7748	Approved
0.6937	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD7115	Discovery
0.6916	Remote Similarity	NPD5959	Approved
0.6915	Remote Similarity	NPD4687	Approved
0.6893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6101	Approved
0.6882	Remote Similarity	NPD5276	Approved
0.6882	Remote Similarity	NPD4243	Approved
0.687	Remote Similarity	NPD6053	Discontinued
0.6852	Remote Similarity	NPD7638	Approved
0.6848	Remote Similarity	NPD4137	Phase 3
0.6837	Remote Similarity	NPD5368	Approved
0.6837	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7525	Registered
0.6832	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7640	Approved
0.6789	Remote Similarity	NPD7639	Approved
0.6774	Remote Similarity	NPD4244	Approved
0.6774	Remote Similarity	NPD4789	Approved
0.6774	Remote Similarity	NPD4245	Approved
0.6768	Remote Similarity	NPD5369	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