NPASS Compound

Structure

NPC197823 OpenBabel07101718242D 31 34 0 0 1 0 0 0 0 0999 V2000 3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1727 -2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1945 -1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5254 -2.6270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 -3.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 16 3 1 1 0 0 0 16 20 1 0 0 0 0 17 28 1 6 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 21 23 1 0 0 0 0 21 26 1 6 0 0 0 22 29 1 1 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 25 27 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.32
Volume:	471.21
LogP:	4.102
LogD:	4.119
LogS:	-4.744
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.846
Fsp3:	0.889
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:	-4.778
MDCK Permeability:	2.599146137072239e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	94.84004974365234%
Volume Distribution (VD):	0.419
Pgp-substrate:	2.0563409328460693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.642

ADMET: Excretion

Clearance (CL):	10.407
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.285
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.821
Carcinogencity:	0.157
Eye Corrosion:	0.006
Eye Irritation:	0.058
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC197823

Natural Product ID:	NPC197823
*Common Name:**	Certonardosterol Q6
IUPAC Name:	(3S,5S,6S,9R,10R,13R,17R)-3,6-dihydroxy-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-15-one
Synonyms:	Certonardosterol Q6
Standard InCHIKey:	ORFDVSJSIHWLNY-WAVJTKCNSA-N
Standard InCHI:	InChI=1S/C27H44O4/c1-15(2)22(29)7-6-16(3)20-14-24(31)25-18-13-23(30)21-12-17(28)8-10-26(21,4)19(18)9-11-27(20,25)5/h15-17,19-23,28-30H,6-14H2,1-5H3/t16-,17+,19+,20-,21-,22+,23+,26-,27-/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1)[C@@H](O)CC1=C3[C@@](CC[C@H]21)(C)[C@H](CC3=O)[C@@H](CC[C@@H](C(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516146
PubChem CID:	21589765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	0.48	ug ml-1	PMID[495172]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[495172]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.17	ug ml-1	PMID[495172]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.22	ug ml-1	PMID[495172]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.43	ug ml-1	PMID[495172]

☑ 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 NPC197823 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	177
0.1-0.2	1319
0.2-0.3	5213
0.3-0.4	14025
0.4-0.5	8418
0.5-0.6	5926
0.6-0.7	4970
0.7-0.8	2367
0.8-0.85	218
0.85-0.9	56
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC250592
0.9518	High Similarity	NPC77263
0.9294	High Similarity	NPC155304
0.9268	High Similarity	NPC470574
0.9059	High Similarity	NPC1015
0.9059	High Similarity	NPC31985
0.9048	High Similarity	NPC475740
0.8966	High Similarity	NPC475255
0.8941	High Similarity	NPC471722
0.8929	High Similarity	NPC474733
0.8929	High Similarity	NPC474732
0.8929	High Similarity	NPC31564
0.8929	High Similarity	NPC145879
0.8929	High Similarity	NPC72133
0.8929	High Similarity	NPC474778
0.8864	High Similarity	NPC245972
0.8864	High Similarity	NPC196485
0.8864	High Similarity	NPC111015
0.8824	High Similarity	NPC58063
0.8736	High Similarity	NPC48010
0.8721	High Similarity	NPC143767
0.8721	High Similarity	NPC328539
0.8721	High Similarity	NPC131470
0.8721	High Similarity	NPC230387
0.8706	High Similarity	NPC471737
0.869	High Similarity	NPC221758
0.869	High Similarity	NPC85774
0.869	High Similarity	NPC214043
0.869	High Similarity	NPC59453
0.8675	High Similarity	NPC151519
0.8652	High Similarity	NPC166906
0.8636	High Similarity	NPC272746
0.8636	High Similarity	NPC168027
0.8636	High Similarity	NPC473998
0.8636	High Similarity	NPC185936
0.8621	High Similarity	NPC474245
0.8621	High Similarity	NPC275740
0.8621	High Similarity	NPC473999
0.8621	High Similarity	NPC186688
0.8621	High Similarity	NPC119416
0.8621	High Similarity	NPC26959
0.8621	High Similarity	NPC309603
0.8621	High Similarity	NPC268406
0.8621	High Similarity	NPC32830
0.8621	High Similarity	NPC86319
0.8605	High Similarity	NPC469314
0.8605	High Similarity	NPC241875
0.8605	High Similarity	NPC138756
0.8605	High Similarity	NPC469317
0.8605	High Similarity	NPC141292
0.8588	High Similarity	NPC469948
0.8571	High Similarity	NPC108078
0.8556	High Similarity	NPC317586
0.8556	High Similarity	NPC200702
0.8556	High Similarity	NPC473170
0.8556	High Similarity	NPC470016
0.8539	High Similarity	NPC12722
0.8523	High Similarity	NPC85173
0.8523	High Similarity	NPC191684
0.8523	High Similarity	NPC183283
0.8523	High Similarity	NPC126993
0.8506	High Similarity	NPC242864
0.8506	High Similarity	NPC471724
0.8506	High Similarity	NPC292491
0.8506	High Similarity	NPC53911
0.8506	High Similarity	NPC474677
0.8506	High Similarity	NPC310752
0.8488	Intermediate Similarity	NPC222613
0.8488	Intermediate Similarity	NPC475022
0.8488	Intermediate Similarity	NPC51014
0.8488	Intermediate Similarity	NPC118648
0.8488	Intermediate Similarity	NPC158393
0.8471	Intermediate Similarity	NPC472265
0.8471	Intermediate Similarity	NPC473246
0.8471	Intermediate Similarity	NPC329043
0.8471	Intermediate Similarity	NPC321187
0.8471	Intermediate Similarity	NPC161423
0.8471	Intermediate Similarity	NPC227064
0.8471	Intermediate Similarity	NPC58841
0.8462	Intermediate Similarity	NPC95565
0.8462	Intermediate Similarity	NPC96859
0.8462	Intermediate Similarity	NPC305483
0.8462	Intermediate Similarity	NPC328162
0.8452	Intermediate Similarity	NPC48362
0.8444	Intermediate Similarity	NPC474690
0.8444	Intermediate Similarity	NPC8993
0.8434	Intermediate Similarity	NPC2482
0.8427	Intermediate Similarity	NPC73457
0.8427	Intermediate Similarity	NPC475806
0.8427	Intermediate Similarity	NPC63748
0.8427	Intermediate Similarity	NPC233116
0.8409	Intermediate Similarity	NPC477943
0.8409	Intermediate Similarity	NPC229871
0.8409	Intermediate Similarity	NPC469319
0.8409	Intermediate Similarity	NPC474704
0.8409	Intermediate Similarity	NPC475921
0.8409	Intermediate Similarity	NPC122116
0.8391	Intermediate Similarity	NPC142361
0.8391	Intermediate Similarity	NPC99909
0.8391	Intermediate Similarity	NPC474684
0.8387	Intermediate Similarity	NPC154072
0.837	Intermediate Similarity	NPC190554
0.837	Intermediate Similarity	NPC18509
0.837	Intermediate Similarity	NPC320306
0.837	Intermediate Similarity	NPC253826
0.8352	Intermediate Similarity	NPC297199
0.8352	Intermediate Similarity	NPC472485
0.8352	Intermediate Similarity	NPC255809
0.8352	Intermediate Similarity	NPC271195
0.8333	Intermediate Similarity	NPC470375
0.8333	Intermediate Similarity	NPC109305
0.8333	Intermediate Similarity	NPC136150
0.8333	Intermediate Similarity	NPC470376
0.8333	Intermediate Similarity	NPC69454
0.8315	Intermediate Similarity	NPC136801
0.8313	Intermediate Similarity	NPC229204
0.8295	Intermediate Similarity	NPC472802
0.8295	Intermediate Similarity	NPC206060
0.8295	Intermediate Similarity	NPC328313
0.8295	Intermediate Similarity	NPC193360
0.8295	Intermediate Similarity	NPC470417
0.828	Intermediate Similarity	NPC114274
0.8276	Intermediate Similarity	NPC327115
0.8276	Intermediate Similarity	NPC20688
0.8276	Intermediate Similarity	NPC155011
0.8276	Intermediate Similarity	NPC56588
0.8276	Intermediate Similarity	NPC28252
0.8276	Intermediate Similarity	NPC472985
0.8276	Intermediate Similarity	NPC94755
0.8276	Intermediate Similarity	NPC472986
0.8276	Intermediate Similarity	NPC55309
0.8261	Intermediate Similarity	NPC249954
0.8261	Intermediate Similarity	NPC7124
0.8261	Intermediate Similarity	NPC192428
0.8261	Intermediate Similarity	NPC471463
0.8256	Intermediate Similarity	NPC82902
0.8256	Intermediate Similarity	NPC237712
0.8256	Intermediate Similarity	NPC33913
0.8242	Intermediate Similarity	NPC299100
0.8242	Intermediate Similarity	NPC472976
0.8242	Intermediate Similarity	NPC212812
0.8242	Intermediate Similarity	NPC474328
0.8242	Intermediate Similarity	NPC472977
0.8242	Intermediate Similarity	NPC23170
0.8235	Intermediate Similarity	NPC212083
0.8222	Intermediate Similarity	NPC158030
0.8222	Intermediate Similarity	NPC4036
0.8222	Intermediate Similarity	NPC65120
0.8222	Intermediate Similarity	NPC86266
0.8222	Intermediate Similarity	NPC110657
0.8222	Intermediate Similarity	NPC131872
0.8222	Intermediate Similarity	NPC99380
0.8222	Intermediate Similarity	NPC473166
0.8222	Intermediate Similarity	NPC235704
0.8222	Intermediate Similarity	NPC233455
0.8222	Intermediate Similarity	NPC189520
0.8222	Intermediate Similarity	NPC212301
0.8222	Intermediate Similarity	NPC145067
0.8222	Intermediate Similarity	NPC23434
0.8222	Intermediate Similarity	NPC248913
0.8222	Intermediate Similarity	NPC472978
0.8202	Intermediate Similarity	NPC472973
0.8202	Intermediate Similarity	NPC472983
0.8202	Intermediate Similarity	NPC76879
0.8191	Intermediate Similarity	NPC144956
0.8191	Intermediate Similarity	NPC316964
0.8191	Intermediate Similarity	NPC15390
0.8191	Intermediate Similarity	NPC88198
0.8191	Intermediate Similarity	NPC157787
0.8191	Intermediate Similarity	NPC327431
0.8182	Intermediate Similarity	NPC93778
0.8182	Intermediate Similarity	NPC73064
0.8182	Intermediate Similarity	NPC317590
0.8182	Intermediate Similarity	NPC159046
0.8182	Intermediate Similarity	NPC233836
0.8182	Intermediate Similarity	NPC187376
0.8182	Intermediate Similarity	NPC477926
0.8182	Intermediate Similarity	NPC90652
0.8172	Intermediate Similarity	NPC151681
0.8172	Intermediate Similarity	NPC18319
0.8172	Intermediate Similarity	NPC122294
0.8172	Intermediate Similarity	NPC175351
0.8172	Intermediate Similarity	NPC121402
0.8172	Intermediate Similarity	NPC43747
0.8172	Intermediate Similarity	NPC224356
0.8172	Intermediate Similarity	NPC474785
0.8172	Intermediate Similarity	NPC132753
0.8172	Intermediate Similarity	NPC474938
0.8161	Intermediate Similarity	NPC76518
0.8161	Intermediate Similarity	NPC133954
0.8161	Intermediate Similarity	NPC471224
0.8161	Intermediate Similarity	NPC474218
0.8152	Intermediate Similarity	NPC139570
0.8152	Intermediate Similarity	NPC280725
0.8152	Intermediate Similarity	NPC318282
0.8152	Intermediate Similarity	NPC469995
0.8152	Intermediate Similarity	NPC259286
0.8152	Intermediate Similarity	NPC174948
0.8152	Intermediate Similarity	NPC88310
0.8152	Intermediate Similarity	NPC180950

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 NPC197823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1696
0.2-0.3	4059
0.3-0.4	2269
0.4-0.5	505
0.5-0.6	166
0.6-0.7	125
0.7-0.8	141
0.8-0.85	29
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD3618	Phase 1
0.8837	High Similarity	NPD5328	Approved
0.869	High Similarity	NPD4786	Approved
0.8675	High Similarity	NPD3667	Approved
0.8636	High Similarity	NPD6079	Approved
0.8539	High Similarity	NPD4202	Approved
0.8471	Intermediate Similarity	NPD3133	Approved
0.8471	Intermediate Similarity	NPD3665	Phase 1
0.8471	Intermediate Similarity	NPD3666	Approved
0.837	Intermediate Similarity	NPD4755	Approved
0.8261	Intermediate Similarity	NPD5221	Approved
0.8261	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5222	Approved
0.8261	Intermediate Similarity	NPD4697	Phase 3
0.8222	Intermediate Similarity	NPD7515	Phase 2
0.8193	Intermediate Similarity	NPD3617	Approved
0.8191	Intermediate Similarity	NPD5286	Approved
0.8191	Intermediate Similarity	NPD4700	Approved
0.8191	Intermediate Similarity	NPD4696	Approved
0.8191	Intermediate Similarity	NPD5285	Approved
0.8172	Intermediate Similarity	NPD5173	Approved
0.8132	Intermediate Similarity	NPD6399	Phase 3
0.8105	Intermediate Similarity	NPD5223	Approved
0.8068	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD5279	Phase 3
0.8046	Intermediate Similarity	NPD3668	Phase 3
0.8021	Intermediate Similarity	NPD5226	Approved
0.8021	Intermediate Similarity	NPD5224	Approved
0.8021	Intermediate Similarity	NPD5211	Phase 2
0.8021	Intermediate Similarity	NPD5225	Approved
0.8021	Intermediate Similarity	NPD4633	Approved
0.8	Intermediate Similarity	NPD4753	Phase 2
0.7959	Intermediate Similarity	NPD6675	Approved
0.7959	Intermediate Similarity	NPD6402	Approved
0.7959	Intermediate Similarity	NPD7128	Approved
0.7959	Intermediate Similarity	NPD5739	Approved
0.7938	Intermediate Similarity	NPD5174	Approved
0.7938	Intermediate Similarity	NPD5175	Approved
0.7938	Intermediate Similarity	NPD4754	Approved
0.7857	Intermediate Similarity	NPD5141	Approved
0.7849	Intermediate Similarity	NPD7748	Approved
0.7816	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4221	Approved
0.78	Intermediate Similarity	NPD6881	Approved
0.78	Intermediate Similarity	NPD7320	Approved
0.78	Intermediate Similarity	NPD6899	Approved
0.7791	Intermediate Similarity	NPD7525	Registered
0.7791	Intermediate Similarity	NPD4695	Discontinued
0.7789	Intermediate Similarity	NPD7902	Approved
0.7778	Intermediate Similarity	NPD4768	Approved
0.7778	Intermediate Similarity	NPD4767	Approved
0.7753	Intermediate Similarity	NPD5329	Approved
0.7753	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD6372	Approved
0.7723	Intermediate Similarity	NPD6373	Approved
0.77	Intermediate Similarity	NPD5701	Approved
0.77	Intermediate Similarity	NPD5697	Approved
0.7683	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6409	Approved
0.7667	Intermediate Similarity	NPD7521	Approved
0.7667	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD7146	Approved
0.7667	Intermediate Similarity	NPD6684	Approved
0.7667	Intermediate Similarity	NPD5330	Approved
0.7654	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6116	Phase 1
0.7647	Intermediate Similarity	NPD7290	Approved
0.7647	Intermediate Similarity	NPD6883	Approved
0.7647	Intermediate Similarity	NPD7102	Approved
0.764	Intermediate Similarity	NPD4197	Approved
0.7624	Intermediate Similarity	NPD6011	Approved
0.7624	Intermediate Similarity	NPD4730	Approved
0.7624	Intermediate Similarity	NPD4729	Approved
0.7624	Intermediate Similarity	NPD5128	Approved
0.7619	Intermediate Similarity	NPD7339	Approved
0.7619	Intermediate Similarity	NPD6942	Approved
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD5210	Approved
0.7579	Intermediate Similarity	NPD4629	Approved
0.7573	Intermediate Similarity	NPD6650	Approved
0.7573	Intermediate Similarity	NPD6617	Approved
0.7573	Intermediate Similarity	NPD6869	Approved
0.7573	Intermediate Similarity	NPD6649	Approved
0.7573	Intermediate Similarity	NPD6847	Approved
0.7573	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD8130	Phase 1
0.7549	Intermediate Similarity	NPD6012	Approved
0.7549	Intermediate Similarity	NPD6014	Approved
0.7549	Intermediate Similarity	NPD6013	Approved
0.7529	Intermediate Similarity	NPD6117	Approved
0.7529	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4788	Approved
0.7526	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5249	Phase 3
0.7476	Intermediate Similarity	NPD5248	Approved
0.7476	Intermediate Similarity	NPD5135	Approved
0.7476	Intermediate Similarity	NPD5169	Approved
0.7476	Intermediate Similarity	NPD5250	Approved
0.7476	Intermediate Similarity	NPD5251	Approved
0.7476	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4634	Approved
0.7476	Intermediate Similarity	NPD5247	Approved
0.7474	Intermediate Similarity	NPD7900	Approved
0.7474	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4688	Approved
0.7473	Intermediate Similarity	NPD4693	Phase 3
0.7473	Intermediate Similarity	NPD5205	Approved
0.7473	Intermediate Similarity	NPD4690	Approved
0.7473	Intermediate Similarity	NPD4138	Approved
0.7473	Intermediate Similarity	NPD4689	Approved
0.7451	Intermediate Similarity	NPD5168	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7447	Intermediate Similarity	NPD8034	Phase 2
0.7447	Intermediate Similarity	NPD8035	Phase 2
0.7412	Intermediate Similarity	NPD3703	Phase 2
0.7404	Intermediate Similarity	NPD5217	Approved
0.7404	Intermediate Similarity	NPD5216	Approved
0.7404	Intermediate Similarity	NPD5215	Approved
0.7404	Intermediate Similarity	NPD5127	Approved
0.7356	Intermediate Similarity	NPD6114	Approved
0.7356	Intermediate Similarity	NPD6697	Approved
0.7356	Intermediate Similarity	NPD6118	Approved
0.7356	Intermediate Similarity	NPD6115	Approved
0.7353	Intermediate Similarity	NPD6412	Phase 2
0.7349	Intermediate Similarity	NPD4245	Approved
0.7349	Intermediate Similarity	NPD4244	Approved
0.7303	Intermediate Similarity	NPD4692	Approved
0.7303	Intermediate Similarity	NPD4139	Approved
0.73	Intermediate Similarity	NPD7632	Discontinued
0.7294	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5280	Approved
0.7283	Intermediate Similarity	NPD4694	Approved
0.7283	Intermediate Similarity	NPD5690	Phase 2
0.7264	Intermediate Similarity	NPD4632	Approved
0.7263	Intermediate Similarity	NPD5281	Approved
0.7263	Intermediate Similarity	NPD5284	Approved
0.7255	Intermediate Similarity	NPD6008	Approved
0.7234	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3698	Phase 2
0.7229	Intermediate Similarity	NPD4137	Phase 3
0.7222	Intermediate Similarity	NPD7115	Discovery
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.7216	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5167	Approved
0.7191	Intermediate Similarity	NPD4748	Discontinued
0.7191	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5696	Approved
0.716	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD4747	Approved
0.7143	Intermediate Similarity	NPD4691	Approved
0.7143	Intermediate Similarity	NPD4789	Approved
0.713	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD6274	Approved
0.7108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5360	Phase 3
0.7097	Intermediate Similarity	NPD4623	Approved
0.7097	Intermediate Similarity	NPD4519	Discontinued
0.7093	Intermediate Similarity	NPD6926	Approved
0.7093	Intermediate Similarity	NPD6924	Approved
0.7091	Intermediate Similarity	NPD7101	Approved
0.7091	Intermediate Similarity	NPD7100	Approved
0.7079	Intermediate Similarity	NPD7645	Phase 2
0.7079	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD6317	Approved
0.7064	Intermediate Similarity	NPD6009	Approved
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7048	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6314	Approved
0.7	Intermediate Similarity	NPD6313	Approved
0.7	Intermediate Similarity	NPD5290	Discontinued
0.6979	Remote Similarity	NPD4096	Approved
0.6966	Remote Similarity	NPD3671	Phase 1
0.6964	Remote Similarity	NPD6908	Approved
0.6964	Remote Similarity	NPD6909	Approved
0.6951	Remote Similarity	NPD7341	Phase 2
0.6947	Remote Similarity	NPD4518	Approved
0.6932	Remote Similarity	NPD6933	Approved
0.6907	Remote Similarity	NPD6411	Approved
0.6903	Remote Similarity	NPD6370	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4058	Approved
0.6887	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6319	Approved
0.686	Remote Similarity	NPD7150	Approved
0.686	Remote Similarity	NPD7152	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