NPASS Compound

Structure

NPC209662 OpenBabel07101719512D 31 34 0 0 1 0 0 0 0 0999 V2000 -6.1235 4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1527 1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 2.4135 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 -5.5054 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 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 2.0000 0.0000 C 0 0 0 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 1 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 19 29 1 6 0 0 0 20 15 1 1 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 6 0 0 0 22 27 1 6 0 0 0 23 28 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 6 0 0 0 25 30 2 0 0 0 0 26 28 1 1 0 0 0 26 31 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.16
Volume:	277.722
LogP:	2.708
LogD:	2.831
LogS:	-4.25
# Rotatable Bonds:	0
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	5.804
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.747
MDCK Permeability:	3.6559296859195456e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.464
Plasma Protein Binding (PPB):	85.4419174194336%
Volume Distribution (VD):	2.11
Pgp-substrate:	10.32568645477295%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	15.838
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.493
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.357
AMES Toxicity:	0.732
Rat Oral Acute Toxicity:	0.278
Maximum Recommended Daily Dose:	0.108
Skin Sensitization:	0.237
Carcinogencity:	0.812
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC209662

Natural Product ID:	NPC209662
*Common Name:**	Gibberoketosterol C
IUPAC Name:	(1S,3R,5S,8S,9S,10R,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-17-[(E,2R)-6-methyl-5-methylidenehept-3-en-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
Synonyms:	gibberoketosterol C
Standard InCHIKey:	SMIJQQDUOZGITI-ROUJNYGZSA-N
Standard InCHI:	InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)21-9-10-22-20-15-25(30)24-13-19(29)14-26(31)28(24,6)23(20)11-12-27(21,22)5/h7-8,16,18-24,26,29,31H,3,9-15H2,1-2,4-6H3/b8-7+/t18-,19-,20+,21-,22+,23+,24-,26+,27-,28-/m1/s1
SMILES:	O[C@H]1C[C@H](O)[C@]2([C@H](C1)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/C(=C)C(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497041
PubChem CID:	16086525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[473009]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[473009]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[473009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30.0	ug.mL-1	PMID[473009]

☑ 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 NPC209662 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	185
0.1-0.2	1038
0.2-0.3	4401
0.3-0.4	10544
0.4-0.5	12533
0.5-0.6	6018
0.6-0.7	5406
0.7-0.8	2343
0.8-0.85	212
0.85-0.9	14
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC191565
0.9205	High Similarity	NPC193360
0.8989	High Similarity	NPC310752
0.8989	High Similarity	NPC292491
0.8936	High Similarity	NPC103051
0.8876	High Similarity	NPC141292
0.8791	High Similarity	NPC46758
0.875	High Similarity	NPC477051
0.875	High Similarity	NPC477053
0.875	High Similarity	NPC477052
0.8696	High Similarity	NPC272746
0.866	High Similarity	NPC477054
0.8617	High Similarity	NPC271195
0.8617	High Similarity	NPC127063
0.8587	High Similarity	NPC126993
0.8571	High Similarity	NPC247957
0.8571	High Similarity	NPC249187
0.8542	High Similarity	NPC119036
0.8539	High Similarity	NPC221758
0.8539	High Similarity	NPC475745
0.8539	High Similarity	NPC59453
0.8539	High Similarity	NPC474482
0.8511	High Similarity	NPC245972
0.8511	High Similarity	NPC474690
0.8511	High Similarity	NPC49670
0.8511	High Similarity	NPC111015
0.8511	High Similarity	NPC196485
0.8495	Intermediate Similarity	NPC131872
0.8495	Intermediate Similarity	NPC473167
0.8478	Intermediate Similarity	NPC475921
0.8478	Intermediate Similarity	NPC474704
0.8478	Intermediate Similarity	NPC84271
0.8478	Intermediate Similarity	NPC77168
0.8478	Intermediate Similarity	NPC186688
0.8478	Intermediate Similarity	NPC1015
0.8478	Intermediate Similarity	NPC31985
0.8478	Intermediate Similarity	NPC102414
0.8462	Intermediate Similarity	NPC475740
0.8462	Intermediate Similarity	NPC136548
0.8462	Intermediate Similarity	NPC142361
0.8462	Intermediate Similarity	NPC58063
0.8462	Intermediate Similarity	NPC474684
0.8444	Intermediate Similarity	NPC470574
0.8444	Intermediate Similarity	NPC474218
0.8438	Intermediate Similarity	NPC190554
0.8438	Intermediate Similarity	NPC108078
0.8427	Intermediate Similarity	NPC113978
0.8427	Intermediate Similarity	NPC472743
0.8427	Intermediate Similarity	NPC475726
0.8421	Intermediate Similarity	NPC88310
0.8421	Intermediate Similarity	NPC279974
0.8421	Intermediate Similarity	NPC180950
0.8404	Intermediate Similarity	NPC134826
0.8404	Intermediate Similarity	NPC12722
0.84	Intermediate Similarity	NPC257353
0.8387	Intermediate Similarity	NPC85173
0.8384	Intermediate Similarity	NPC312900
0.837	Intermediate Similarity	NPC328539
0.837	Intermediate Similarity	NPC474677
0.837	Intermediate Similarity	NPC471722
0.8352	Intermediate Similarity	NPC74363
0.8352	Intermediate Similarity	NPC474732
0.8352	Intermediate Similarity	NPC145879
0.8352	Intermediate Similarity	NPC31564
0.8352	Intermediate Similarity	NPC472738
0.8352	Intermediate Similarity	NPC51014
0.8352	Intermediate Similarity	NPC475862
0.8352	Intermediate Similarity	NPC473168
0.8352	Intermediate Similarity	NPC474733
0.8352	Intermediate Similarity	NPC72133
0.8352	Intermediate Similarity	NPC213412
0.8352	Intermediate Similarity	NPC94755
0.8352	Intermediate Similarity	NPC474778
0.8333	Intermediate Similarity	NPC214043
0.8333	Intermediate Similarity	NPC49371
0.8333	Intermediate Similarity	NPC474493
0.8333	Intermediate Similarity	NPC78473
0.8333	Intermediate Similarity	NPC471153
0.8333	Intermediate Similarity	NPC85774
0.8333	Intermediate Similarity	NPC82902
0.8316	Intermediate Similarity	NPC299100
0.8316	Intermediate Similarity	NPC471207
0.8315	Intermediate Similarity	NPC151519
0.83	Intermediate Similarity	NPC72255
0.8298	Intermediate Similarity	NPC212301
0.8298	Intermediate Similarity	NPC475806
0.8298	Intermediate Similarity	NPC233116
0.8298	Intermediate Similarity	NPC86266
0.8298	Intermediate Similarity	NPC110657
0.8283	Intermediate Similarity	NPC193934
0.8283	Intermediate Similarity	NPC271980
0.828	Intermediate Similarity	NPC119416
0.828	Intermediate Similarity	NPC309603
0.828	Intermediate Similarity	NPC128496
0.828	Intermediate Similarity	NPC86319
0.828	Intermediate Similarity	NPC275740
0.828	Intermediate Similarity	NPC474245
0.828	Intermediate Similarity	NPC473999
0.828	Intermediate Similarity	NPC32830
0.8265	Intermediate Similarity	NPC15390
0.8265	Intermediate Similarity	NPC154072
0.8261	Intermediate Similarity	NPC93778
0.8261	Intermediate Similarity	NPC153604
0.8261	Intermediate Similarity	NPC90652
0.8261	Intermediate Similarity	NPC73064
0.8261	Intermediate Similarity	NPC159046
0.8261	Intermediate Similarity	NPC233836
0.8261	Intermediate Similarity	NPC187376
0.8247	Intermediate Similarity	NPC474785
0.8247	Intermediate Similarity	NPC474938
0.8242	Intermediate Similarity	NPC471224
0.8242	Intermediate Similarity	NPC292553
0.8242	Intermediate Similarity	NPC76518
0.8242	Intermediate Similarity	NPC190704
0.8242	Intermediate Similarity	NPC471034
0.8242	Intermediate Similarity	NPC133954
0.8229	Intermediate Similarity	NPC472485
0.8229	Intermediate Similarity	NPC162001
0.8229	Intermediate Similarity	NPC222845
0.8229	Intermediate Similarity	NPC45324
0.8222	Intermediate Similarity	NPC477818
0.8211	Intermediate Similarity	NPC107674
0.8211	Intermediate Similarity	NPC475255
0.8211	Intermediate Similarity	NPC170220
0.8211	Intermediate Similarity	NPC470376
0.8211	Intermediate Similarity	NPC244356
0.8211	Intermediate Similarity	NPC470224
0.8211	Intermediate Similarity	NPC224060
0.8211	Intermediate Similarity	NPC470375
0.8211	Intermediate Similarity	NPC141497
0.8211	Intermediate Similarity	NPC477855
0.8202	Intermediate Similarity	NPC470383
0.82	Intermediate Similarity	NPC222153
0.82	Intermediate Similarity	NPC191892
0.8191	Intermediate Similarity	NPC261994
0.8191	Intermediate Similarity	NPC48010
0.8191	Intermediate Similarity	NPC149761
0.8191	Intermediate Similarity	NPC470378
0.8191	Intermediate Similarity	NPC191684
0.8182	Intermediate Similarity	NPC474113
0.8182	Intermediate Similarity	NPC215843
0.8172	Intermediate Similarity	NPC471724
0.8172	Intermediate Similarity	NPC328313
0.8172	Intermediate Similarity	NPC472739
0.8172	Intermediate Similarity	NPC53911
0.8172	Intermediate Similarity	NPC474719
0.8172	Intermediate Similarity	NPC131470
0.8172	Intermediate Similarity	NPC44181
0.8172	Intermediate Similarity	NPC470417
0.8172	Intermediate Similarity	NPC143767
0.8172	Intermediate Similarity	NPC472802
0.8163	Intermediate Similarity	NPC114274
0.8161	Intermediate Similarity	NPC472746
0.8152	Intermediate Similarity	NPC89077
0.8152	Intermediate Similarity	NPC222613
0.8152	Intermediate Similarity	NPC6605
0.8152	Intermediate Similarity	NPC55309
0.8152	Intermediate Similarity	NPC118648
0.8152	Intermediate Similarity	NPC155011
0.8152	Intermediate Similarity	NPC201273
0.8152	Intermediate Similarity	NPC269058
0.8152	Intermediate Similarity	NPC71520
0.8152	Intermediate Similarity	NPC475022
0.8152	Intermediate Similarity	NPC469994
0.8152	Intermediate Similarity	NPC28252
0.8144	Intermediate Similarity	NPC301534
0.8144	Intermediate Similarity	NPC160056
0.8144	Intermediate Similarity	NPC250757
0.8137	Intermediate Similarity	NPC477916
0.8132	Intermediate Similarity	NPC474233
0.8132	Intermediate Similarity	NPC146683
0.8132	Intermediate Similarity	NPC264665
0.8132	Intermediate Similarity	NPC473246
0.8132	Intermediate Similarity	NPC74595
0.8125	Intermediate Similarity	NPC469406
0.8125	Intermediate Similarity	NPC103527
0.8125	Intermediate Similarity	NPC261333
0.8125	Intermediate Similarity	NPC292374
0.8125	Intermediate Similarity	NPC215271
0.8125	Intermediate Similarity	NPC104371
0.8125	Intermediate Similarity	NPC159365
0.8125	Intermediate Similarity	NPC29247
0.8125	Intermediate Similarity	NPC8993
0.8125	Intermediate Similarity	NPC129004
0.8125	Intermediate Similarity	NPC80365
0.8125	Intermediate Similarity	NPC292793
0.8125	Intermediate Similarity	NPC101233
0.8125	Intermediate Similarity	NPC289539
0.8125	Intermediate Similarity	NPC153775
0.8125	Intermediate Similarity	NPC111524
0.8125	Intermediate Similarity	NPC91772
0.8119	Intermediate Similarity	NPC201763
0.8119	Intermediate Similarity	NPC29705
0.8111	Intermediate Similarity	NPC48362
0.8105	Intermediate Similarity	NPC301244
0.8105	Intermediate Similarity	NPC299185
0.8105	Intermediate Similarity	NPC185936
0.8105	Intermediate Similarity	NPC475708
0.8105	Intermediate Similarity	NPC19114
0.8105	Intermediate Similarity	NPC473998

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 NPC209662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1251
0.2-0.3	3882
0.3-0.4	2577
0.4-0.5	782
0.5-0.6	182
0.6-0.7	147
0.7-0.8	166
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD3618	Phase 1
0.8539	High Similarity	NPD4786	Approved
0.8495	Intermediate Similarity	NPD6079	Approved
0.8478	Intermediate Similarity	NPD5328	Approved
0.8315	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD4202	Approved
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7959	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD5222	Approved
0.7957	Intermediate Similarity	NPD5279	Phase 3
0.7935	Intermediate Similarity	NPD3666	Approved
0.7935	Intermediate Similarity	NPD3133	Approved
0.7935	Intermediate Similarity	NPD3665	Phase 1
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.7889	Intermediate Similarity	NPD7525	Registered
0.7879	Intermediate Similarity	NPD4755	Approved
0.7879	Intermediate Similarity	NPD5173	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD6929	Approved
0.7753	Intermediate Similarity	NPD6932	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD5226	Approved
0.7732	Intermediate Similarity	NPD7515	Phase 2
0.7723	Intermediate Similarity	NPD4700	Approved
0.7708	Intermediate Similarity	NPD4753	Phase 2
0.7692	Intermediate Similarity	NPD6930	Phase 2
0.7692	Intermediate Similarity	NPD6931	Approved
0.7677	Intermediate Similarity	NPD5210	Approved
0.7677	Intermediate Similarity	NPD4629	Approved
0.767	Intermediate Similarity	NPD5174	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.7667	Intermediate Similarity	NPD7145	Approved
0.7647	Intermediate Similarity	NPD5223	Approved
0.7634	Intermediate Similarity	NPD4788	Approved
0.7624	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7586	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD4634	Approved
0.7556	Intermediate Similarity	NPD5776	Phase 2
0.7556	Intermediate Similarity	NPD6925	Approved
0.7553	Intermediate Similarity	NPD3668	Phase 3
0.7551	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD8034	Phase 2
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7528	Intermediate Similarity	NPD3703	Phase 2
0.7528	Intermediate Similarity	NPD7339	Approved
0.7528	Intermediate Similarity	NPD6942	Approved
0.7527	Intermediate Similarity	NPD4223	Phase 3
0.7527	Intermediate Similarity	NPD4221	Approved
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7474	Intermediate Similarity	NPD5329	Approved
0.7473	Intermediate Similarity	NPD6697	Approved
0.7473	Intermediate Similarity	NPD6115	Approved
0.7473	Intermediate Similarity	NPD6118	Approved
0.7473	Intermediate Similarity	NPD6114	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7447	Intermediate Similarity	NPD6695	Phase 3
0.7419	Intermediate Similarity	NPD6902	Approved
0.7416	Intermediate Similarity	NPD6926	Approved
0.7416	Intermediate Similarity	NPD6924	Approved
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.74	Intermediate Similarity	NPD7748	Approved
0.7396	Intermediate Similarity	NPD4694	Approved
0.7396	Intermediate Similarity	NPD5280	Approved
0.7396	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6683	Phase 2
0.7391	Intermediate Similarity	NPD7645	Phase 2
0.7386	Intermediate Similarity	NPD7151	Approved
0.7386	Intermediate Similarity	NPD7150	Approved
0.7386	Intermediate Similarity	NPD7152	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD7637	Suspended
0.7368	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4197	Approved
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7356	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7353	Intermediate Similarity	NPD7902	Approved
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD4754	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7312	Intermediate Similarity	NPD7332	Phase 2
0.7292	Intermediate Similarity	NPD6893	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD7143	Approved
0.7273	Intermediate Similarity	NPD7144	Approved
0.7253	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6933	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7245	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD5168	Approved
0.7216	Intermediate Similarity	NPD4690	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD4688	Approved
0.7216	Intermediate Similarity	NPD4689	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD4138	Approved
0.7216	Intermediate Similarity	NPD5205	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD4693	Phase 3
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD5690	Phase 2
0.7207	Intermediate Similarity	NPD4632	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD5215	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7159	Intermediate Similarity	NPD6922	Approved
0.7159	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7143	Intermediate Similarity	NPD7524	Approved
0.713	Intermediate Similarity	NPD6054	Approved
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7115	Intermediate Similarity	NPD5696	Approved
0.7097	Intermediate Similarity	NPD3617	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5135	Approved
0.7079	Intermediate Similarity	NPD4245	Approved
0.7079	Intermediate Similarity	NPD4244	Approved
0.7079	Intermediate Similarity	NPD4789	Approved
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7900	Approved
0.7053	Intermediate Similarity	NPD6898	Phase 1
0.7045	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5360	Phase 3
0.7037	Intermediate Similarity	NPD7333	Discontinued
0.7037	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD4687	Approved
0.7033	Intermediate Similarity	NPD5733	Approved
0.7033	Intermediate Similarity	NPD4058	Approved
0.703	Intermediate Similarity	NPD6411	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7027	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4195	Approved
0.7018	Intermediate Similarity	NPD6009	Approved
0.7009	Intermediate Similarity	NPD6370	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5695	Phase 3
0.6983	Remote Similarity	NPD6059	Approved
0.6983	Remote Similarity	NPD6319	Approved
0.697	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3698	Phase 2
0.6947	Remote Similarity	NPD7509	Discontinued
0.6931	Remote Similarity	NPD5207	Approved
0.6931	Remote Similarity	NPD4096	Approved
0.693	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6916	Remote Similarity	NPD7632	Discontinued
0.6915	Remote Similarity	NPD5784	Clinical (unspecified phase)

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