NPASS Compound

Structure

NPC193870 OpenBabel07101718202D 32 35 0 0 1 0 0 0 0 0999 V2000 4.1945 1.8838 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 4.8126 3.7859 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 2.5472 2.4190 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 -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 3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 2.6270 0.0000 C 0 0 2 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 3.8344 3.5780 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 2 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 -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 2 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 -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 3.4743 5.2722 0.0000 O 0 0 0 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 -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 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 6 0 0 0 16 18 1 0 0 0 0 17 2 1 6 0 0 0 17 22 1 0 0 0 0 18 3 1 1 0 0 0 19 30 1 1 0 0 0 20 13 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 1 0 0 0 22 28 1 1 0 0 0 23 24 1 0 0 0 0 23 27 1 1 0 0 0 24 31 1 6 0 0 0 25 26 1 0 0 0 0 25 32 1 1 0 0 0 26 28 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.36
Volume:	491.143
LogP:	4.753
LogD:	4.636
LogS:	-4.278
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	5.107
Fsp3:	0.929
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:	-4.991
MDCK Permeability:	7.323230238398537e-05
Pgp-inhibitor:	0.93
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.602
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	86.06490325927734%
Volume Distribution (VD):	0.756
Pgp-substrate:	1.6253818273544312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.477
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	3.091
Half-life (T1/2):	0.497

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.344
Maximum Recommended Daily Dose:	0.349
Skin Sensitization:	0.912
Carcinogencity:	0.028
Eye Corrosion:	0.014
Eye Irritation:	0.159
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC193870

Natural Product ID:	NPC193870
*Common Name:**	Certonardosterol D4
IUPAC Name:	(3S,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(E,2R,5R,6S)-7-hydroxy-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6,15-triol
Synonyms:	Certonardosterol D4
Standard InCHIKey:	DUCRVTKCYSCQLO-FMDNLKLDSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-16(18(3)15-29)6-7-17(2)22-14-25(32)26-20-13-24(31)23-12-19(30)8-10-27(23,4)21(20)9-11-28(22,26)5/h6-7,16-26,29-32H,8-15H2,1-5H3/b7-6+/t16-,17-,18-,19+,20-,21+,22-,23-,24+,25-,26-,27-,28-/m1/s1
SMILES:	C[C@H](/C=C/[C@@H](C)[C@H]1C[C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465355
PubChem CID:	11419512
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
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
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.75	ug ml-1	PMID[527349]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	1.51	ug ml-1	PMID[527349]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.48	ug ml-1	PMID[527349]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	1.22	ug ml-1	PMID[527349]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	1.25	ug ml-1	PMID[527349]

☑ 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 NPC193870 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	1480
0.2-0.3	6555
0.3-0.4	15855
0.4-0.5	7397
0.5-0.6	4781
0.6-0.7	4604
0.7-0.8	1568
0.8-0.85	195
0.85-0.9	52
0.9-0.95	23
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141941
0.9872	High Similarity	NPC127606
0.9872	High Similarity	NPC475798
0.9744	High Similarity	NPC477818
0.9744	High Similarity	NPC110778
0.9625	High Similarity	NPC6605
0.9625	High Similarity	NPC139724
0.9506	High Similarity	NPC474657
0.9506	High Similarity	NPC186145
0.939	High Similarity	NPC475664
0.9383	High Similarity	NPC24277
0.9383	High Similarity	NPC201273
0.9375	High Similarity	NPC124172
0.9277	High Similarity	NPC109744
0.9167	High Similarity	NPC473956
0.9167	High Similarity	NPC475751
0.9136	High Similarity	NPC209802
0.9125	High Similarity	NPC470614
0.9125	High Similarity	NPC1272
0.9114	High Similarity	NPC236237
0.9114	High Similarity	NPC102253
0.9114	High Similarity	NPC71535
0.9114	High Similarity	NPC322313
0.9114	High Similarity	NPC78545
0.9103	High Similarity	NPC6978
0.9103	High Similarity	NPC167037
0.9103	High Similarity	NPC244385
0.9103	High Similarity	NPC477817
0.9103	High Similarity	NPC138621
0.9103	High Similarity	NPC477819
0.9048	High Similarity	NPC105495
0.8987	High Similarity	NPC80530
0.8987	High Similarity	NPC1319
0.8987	High Similarity	NPC273410
0.8961	High Similarity	NPC103822
0.8929	High Similarity	NPC470542
0.8875	High Similarity	NPC26117
0.8861	High Similarity	NPC285761
0.8846	High Similarity	NPC237460
0.8795	High Similarity	NPC318390
0.878	High Similarity	NPC113978
0.878	High Similarity	NPC207013
0.878	High Similarity	NPC232023
0.875	High Similarity	NPC472463
0.875	High Similarity	NPC24504
0.869	High Similarity	NPC299068
0.869	High Similarity	NPC261266
0.8675	High Similarity	NPC474493
0.8675	High Similarity	NPC255882
0.8659	High Similarity	NPC218616
0.8659	High Similarity	NPC248886
0.8659	High Similarity	NPC296701
0.8642	High Similarity	NPC13554
0.8642	High Similarity	NPC47149
0.8625	High Similarity	NPC148977
0.8625	High Similarity	NPC65897
0.8625	High Similarity	NPC475
0.8625	High Similarity	NPC85346
0.8625	High Similarity	NPC87604
0.8625	High Similarity	NPC477522
0.8625	High Similarity	NPC472500
0.8625	High Similarity	NPC302041
0.8625	High Similarity	NPC472502
0.8625	High Similarity	NPC472499
0.8608	High Similarity	NPC134330
0.8608	High Similarity	NPC129165
0.8608	High Similarity	NPC189883
0.859	High Similarity	NPC308440
0.859	High Similarity	NPC472503
0.8588	High Similarity	NPC271967
0.8571	High Similarity	NPC470360
0.8556	High Similarity	NPC477226
0.8554	High Similarity	NPC470558
0.8554	High Similarity	NPC134481
0.8554	High Similarity	NPC82623
0.8537	High Similarity	NPC470383
0.8519	High Similarity	NPC476316
0.85	High Similarity	NPC471798
0.85	High Similarity	NPC138502
0.85	High Similarity	NPC214570
0.85	High Similarity	NPC202540
0.8488	Intermediate Similarity	NPC4574
0.8488	Intermediate Similarity	NPC212596
0.8488	Intermediate Similarity	NPC2158
0.8488	Intermediate Similarity	NPC133588
0.8488	Intermediate Similarity	NPC475605
0.8481	Intermediate Similarity	NPC3403
0.8481	Intermediate Similarity	NPC257347
0.8481	Intermediate Similarity	NPC471723
0.8481	Intermediate Similarity	NPC141071
0.8471	Intermediate Similarity	NPC269058
0.8471	Intermediate Similarity	NPC6391
0.8471	Intermediate Similarity	NPC152808
0.8471	Intermediate Similarity	NPC121981
0.8471	Intermediate Similarity	NPC71520
0.8471	Intermediate Similarity	NPC293287
0.8452	Intermediate Similarity	NPC256567
0.8452	Intermediate Similarity	NPC469878
0.8452	Intermediate Similarity	NPC478102
0.8444	Intermediate Similarity	NPC253115
0.8444	Intermediate Similarity	NPC304899
0.8442	Intermediate Similarity	NPC63588
0.8442	Intermediate Similarity	NPC251201
0.8442	Intermediate Similarity	NPC232925
0.8434	Intermediate Similarity	NPC20853
0.8434	Intermediate Similarity	NPC50964
0.8434	Intermediate Similarity	NPC30166
0.8434	Intermediate Similarity	NPC201852
0.8427	Intermediate Similarity	NPC111015
0.8415	Intermediate Similarity	NPC236112
0.8415	Intermediate Similarity	NPC475679
0.8409	Intermediate Similarity	NPC41554
0.8409	Intermediate Similarity	NPC97404
0.8409	Intermediate Similarity	NPC275671
0.8395	Intermediate Similarity	NPC42853
0.8395	Intermediate Similarity	NPC11908
0.8395	Intermediate Similarity	NPC275910
0.8395	Intermediate Similarity	NPC312328
0.8395	Intermediate Similarity	NPC31828
0.8395	Intermediate Similarity	NPC477514
0.8395	Intermediate Similarity	NPC301707
0.8391	Intermediate Similarity	NPC101886
0.8375	Intermediate Similarity	NPC240604
0.8375	Intermediate Similarity	NPC14112
0.8375	Intermediate Similarity	NPC321016
0.8375	Intermediate Similarity	NPC107059
0.8375	Intermediate Similarity	NPC96319
0.8375	Intermediate Similarity	NPC202642
0.8375	Intermediate Similarity	NPC300324
0.8375	Intermediate Similarity	NPC470362
0.8375	Intermediate Similarity	NPC73875
0.8375	Intermediate Similarity	NPC86305
0.8375	Intermediate Similarity	NPC46160
0.8375	Intermediate Similarity	NPC113733
0.8375	Intermediate Similarity	NPC38141
0.8375	Intermediate Similarity	NPC321381
0.8372	Intermediate Similarity	NPC304083
0.8353	Intermediate Similarity	NPC22133
0.8352	Intermediate Similarity	NPC190554
0.8333	Intermediate Similarity	NPC216420
0.8333	Intermediate Similarity	NPC85095
0.8333	Intermediate Similarity	NPC111234
0.8333	Intermediate Similarity	NPC211135
0.8315	Intermediate Similarity	NPC98193
0.8313	Intermediate Similarity	NPC209620
0.8313	Intermediate Similarity	NPC476646
0.8313	Intermediate Similarity	NPC23852
0.8313	Intermediate Similarity	NPC157655
0.8313	Intermediate Similarity	NPC474531
0.8312	Intermediate Similarity	NPC477820
0.8295	Intermediate Similarity	NPC329596
0.8295	Intermediate Similarity	NPC107189
0.8295	Intermediate Similarity	NPC3345
0.8295	Intermediate Similarity	NPC291484
0.8295	Intermediate Similarity	NPC295668
0.8295	Intermediate Similarity	NPC11216
0.8295	Intermediate Similarity	NPC80561
0.8295	Intermediate Similarity	NPC204188
0.8293	Intermediate Similarity	NPC30986
0.8293	Intermediate Similarity	NPC49627
0.8293	Intermediate Similarity	NPC475727
0.8293	Intermediate Similarity	NPC80297
0.8293	Intermediate Similarity	NPC209430
0.8293	Intermediate Similarity	NPC472742
0.8293	Intermediate Similarity	NPC49599
0.8293	Intermediate Similarity	NPC116119
0.8276	Intermediate Similarity	NPC67872
0.8276	Intermediate Similarity	NPC471952
0.8276	Intermediate Similarity	NPC474668
0.8276	Intermediate Similarity	NPC193360
0.8272	Intermediate Similarity	NPC318495
0.8272	Intermediate Similarity	NPC155986
0.8272	Intermediate Similarity	NPC307336
0.8272	Intermediate Similarity	NPC198968
0.8272	Intermediate Similarity	NPC260301
0.8272	Intermediate Similarity	NPC130136
0.8256	Intermediate Similarity	NPC94462
0.825	Intermediate Similarity	NPC22105
0.825	Intermediate Similarity	NPC185536
0.825	Intermediate Similarity	NPC291503
0.825	Intermediate Similarity	NPC240235
0.825	Intermediate Similarity	NPC136188
0.825	Intermediate Similarity	NPC178383
0.825	Intermediate Similarity	NPC121744
0.825	Intermediate Similarity	NPC118508
0.825	Intermediate Similarity	NPC28657
0.825	Intermediate Similarity	NPC230704
0.825	Intermediate Similarity	NPC285893
0.825	Intermediate Similarity	NPC322353
0.825	Intermediate Similarity	NPC231256
0.825	Intermediate Similarity	NPC162742
0.825	Intermediate Similarity	NPC134847
0.825	Intermediate Similarity	NPC70982
0.825	Intermediate Similarity	NPC304309
0.825	Intermediate Similarity	NPC104387
0.825	Intermediate Similarity	NPC212879
0.825	Intermediate Similarity	NPC288035
0.825	Intermediate Similarity	NPC230301
0.8242	Intermediate Similarity	NPC471903
0.8235	Intermediate Similarity	NPC205845

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 NPC193870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1720
0.2-0.3	4485
0.3-0.4	1988
0.4-0.5	359
0.5-0.6	164
0.6-0.7	167
0.7-0.8	105
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9114	High Similarity	NPD7525	Registered
0.8375	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6942	Approved
0.825	Intermediate Similarity	NPD7339	Approved
0.7955	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4785	Approved
0.7901	Intermediate Similarity	NPD4784	Approved
0.7875	Intermediate Similarity	NPD4243	Approved
0.7857	Intermediate Similarity	NPD7645	Phase 2
0.7717	Intermediate Similarity	NPD4202	Approved
0.7684	Intermediate Similarity	NPD7638	Approved
0.7683	Intermediate Similarity	NPD6924	Approved
0.7683	Intermediate Similarity	NPD6926	Approved
0.7654	Intermediate Similarity	NPD7150	Approved
0.7654	Intermediate Similarity	NPD7152	Approved
0.7654	Intermediate Similarity	NPD7151	Approved
0.7647	Intermediate Similarity	NPD6929	Approved
0.7619	Intermediate Similarity	NPD6932	Approved
0.7614	Intermediate Similarity	NPD4786	Approved
0.7614	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6079	Approved
0.7604	Intermediate Similarity	NPD7639	Approved
0.7604	Intermediate Similarity	NPD5285	Approved
0.7604	Intermediate Similarity	NPD5286	Approved
0.7604	Intermediate Similarity	NPD7640	Approved
0.7604	Intermediate Similarity	NPD4696	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7579	Intermediate Similarity	NPD4755	Approved
0.7558	Intermediate Similarity	NPD6930	Phase 2
0.7558	Intermediate Similarity	NPD4748	Discontinued
0.7558	Intermediate Similarity	NPD6931	Approved
0.7531	Intermediate Similarity	NPD7143	Approved
0.7531	Intermediate Similarity	NPD7144	Approved
0.7529	Intermediate Similarity	NPD7145	Approved
0.7526	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7449	Intermediate Similarity	NPD5224	Approved
0.7449	Intermediate Similarity	NPD5211	Phase 2
0.7449	Intermediate Similarity	NPD4633	Approved
0.7449	Intermediate Similarity	NPD5225	Approved
0.7449	Intermediate Similarity	NPD5226	Approved
0.7444	Intermediate Similarity	NPD3618	Phase 1
0.7442	Intermediate Similarity	NPD4195	Approved
0.7423	Intermediate Similarity	NPD4700	Approved
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7416	Intermediate Similarity	NPD3666	Approved
0.7412	Intermediate Similarity	NPD5776	Phase 2
0.7412	Intermediate Similarity	NPD6925	Approved
0.7407	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6923	Approved
0.7407	Intermediate Similarity	NPD6922	Approved
0.7386	Intermediate Similarity	NPD3667	Approved
0.7381	Intermediate Similarity	NPD5275	Approved
0.7381	Intermediate Similarity	NPD4190	Phase 3
0.7374	Intermediate Similarity	NPD5174	Approved
0.7374	Intermediate Similarity	NPD5175	Approved
0.7356	Intermediate Similarity	NPD7509	Discontinued
0.7356	Intermediate Similarity	NPD7514	Phase 3
0.7333	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4787	Phase 1
0.73	Intermediate Similarity	NPD5141	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD6902	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7241	Intermediate Similarity	NPD6683	Phase 2
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD4753	Phase 2
0.72	Intermediate Similarity	NPD4754	Approved
0.7174	Intermediate Similarity	NPD7524	Approved
0.7174	Intermediate Similarity	NPD7750	Discontinued
0.7159	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD6928	Phase 2
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7157	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD6893	Approved
0.7126	Intermediate Similarity	NPD6114	Approved
0.7126	Intermediate Similarity	NPD6115	Approved
0.7126	Intermediate Similarity	NPD6118	Approved
0.7126	Intermediate Similarity	NPD6697	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7111	Intermediate Similarity	NPD4788	Approved
0.7087	Intermediate Similarity	NPD6011	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD4730	Approved
0.7087	Intermediate Similarity	NPD4729	Approved
0.7075	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7019	Intermediate Similarity	NPD6012	Approved
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6013	Approved
0.7019	Intermediate Similarity	NPD6014	Approved
0.7011	Intermediate Similarity	NPD6116	Phase 1
0.701	Intermediate Similarity	NPD5210	Approved
0.701	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.699	Remote Similarity	NPD5701	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.6957	Remote Similarity	NPD5329	Approved
0.6952	Remote Similarity	NPD5251	Approved
0.6952	Remote Similarity	NPD5250	Approved
0.6952	Remote Similarity	NPD5249	Phase 3
0.6952	Remote Similarity	NPD5248	Approved
0.6952	Remote Similarity	NPD5169	Approved
0.6952	Remote Similarity	NPD5247	Approved
0.6952	Remote Similarity	NPD5135	Approved
0.6952	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD5128	Approved
0.6909	Remote Similarity	NPD7516	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6889	Remote Similarity	NPD6898	Phase 1
0.6887	Remote Similarity	NPD5215	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5217	Approved
0.6887	Remote Similarity	NPD5127	Approved
0.6887	Remote Similarity	NPD5216	Approved
0.6881	Remote Similarity	NPD6009	Approved
0.6875	Remote Similarity	NPD7087	Discontinued
0.6869	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD6084	Phase 2
0.6848	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD4197	Approved
0.6847	Remote Similarity	NPD6054	Approved
0.6847	Remote Similarity	NPD8294	Approved
0.6847	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6827	Remote Similarity	NPD6412	Phase 2
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5290	Discontinued
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6782	Remote Similarity	NPD3703	Phase 2
0.6782	Remote Similarity	NPD8264	Approved
0.6737	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7748	Approved
0.6731	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD6370	Approved
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6701	Remote Similarity	NPD7637	Suspended
0.6701	Remote Similarity	NPD5284	Approved
0.6701	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD7902	Approved
0.6697	Remote Similarity	NPD5167	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5983	Phase 2
0.6637	Remote Similarity	NPD6015	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