NPASS Compound

Structure

NPC127606 OpenBabel07101719132D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.8126 3.7859 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 -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 -3.8344 3.5780 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 -3.5254 2.6270 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 -5.1727 2.0917 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 6 7 2 0 0 0 0 6 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 18 1 0 0 0 0 17 3 1 1 0 0 0 17 22 1 0 0 0 0 18 7 1 6 0 0 0 19 30 1 6 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 6 0 0 0 22 28 1 6 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 24 31 1 1 0 0 0 25 26 1 0 0 0 0 25 32 1 6 0 0 0 26 28 1 6 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.36
Volume:	491.143
LogP:	4.724
LogD:	4.629
LogS:	-4.3
# 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:	5.077
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:	-4.99
MDCK Permeability:	7.082729280227795e-05
Pgp-inhibitor:	0.386
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.518
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	85.0313949584961%
Volume Distribution (VD):	0.923
Pgp-substrate:	1.7005341053009033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.298
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.604

ADMET: Excretion

Clearance (CL):	2.882
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.881
Carcinogencity:	0.019
Eye Corrosion:	0.007
Eye Irritation:	0.114
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC127606

Natural Product ID:	NPC127606
*Common Name:**	Certonardosterol D2
IUPAC Name:	(3S,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(E,2R,5R)-5-(hydroxymethyl)-6-methylhept-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 D2
Standard InCHIKey:	OPELMUKUWKWTPN-QQGCWHOWSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-16(2)18(15-29)7-6-17(3)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+/t17-,18-,19+,20-,21+,22-,23-,24+,25-,26-,27-,28-/m1/s1
SMILES:	CC(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)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518378
PubChem CID:	11396724
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	=	0.15	ug ml-1	PMID[523537]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	0.08	ug ml-1	PMID[523537]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.09	ug ml-1	PMID[523537]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.07	ug ml-1	PMID[523537]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	0.01	ug ml-1	PMID[523537]

☑ 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 NPC127606 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	1454
0.2-0.3	6094
0.3-0.4	15858
0.4-0.5	7686
0.5-0.6	4931
0.6-0.7	4639
0.7-0.8	1572
0.8-0.85	207
0.85-0.9	45
0.9-0.95	22
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475798
0.9872	High Similarity	NPC193870
0.9872	High Similarity	NPC141941
0.962	High Similarity	NPC477818
0.962	High Similarity	NPC110778
0.9512	High Similarity	NPC475664
0.9506	High Similarity	NPC139724
0.9506	High Similarity	NPC24277
0.9506	High Similarity	NPC6605
0.95	High Similarity	NPC124172
0.939	High Similarity	NPC186145
0.939	High Similarity	NPC474657
0.9286	High Similarity	NPC475751
0.9286	High Similarity	NPC473956
0.9268	High Similarity	NPC201273
0.9259	High Similarity	NPC209802
0.925	High Similarity	NPC1272
0.925	High Similarity	NPC470614
0.9241	High Similarity	NPC78545
0.9241	High Similarity	NPC71535
0.9167	High Similarity	NPC105495
0.9167	High Similarity	NPC109744
0.9048	High Similarity	NPC470542
0.9	High Similarity	NPC322313
0.9	High Similarity	NPC102253
0.9	High Similarity	NPC26117
0.9	High Similarity	NPC236237
0.8987	High Similarity	NPC244385
0.8987	High Similarity	NPC477817
0.8987	High Similarity	NPC477819
0.8987	High Similarity	NPC6978
0.8987	High Similarity	NPC167037
0.8987	High Similarity	NPC138621
0.8902	High Similarity	NPC232023
0.8875	High Similarity	NPC80530
0.8875	High Similarity	NPC273410
0.8875	High Similarity	NPC1319
0.8875	High Similarity	NPC472463
0.8846	High Similarity	NPC103822
0.881	High Similarity	NPC261266
0.8795	High Similarity	NPC474493
0.8795	High Similarity	NPC255882
0.878	High Similarity	NPC248886
0.8765	High Similarity	NPC47149
0.875	High Similarity	NPC148977
0.875	High Similarity	NPC285761
0.875	High Similarity	NPC477522
0.875	High Similarity	NPC87604
0.8734	High Similarity	NPC237460
0.8706	High Similarity	NPC271967
0.869	High Similarity	NPC318390
0.8675	High Similarity	NPC207013
0.8675	High Similarity	NPC113978
0.8659	High Similarity	NPC470383
0.8642	High Similarity	NPC24504
0.8625	High Similarity	NPC471798
0.8605	High Similarity	NPC2158
0.8588	High Similarity	NPC121981
0.8588	High Similarity	NPC152808
0.8588	High Similarity	NPC293287
0.8588	High Similarity	NPC6391
0.8588	High Similarity	NPC299068
0.8571	High Similarity	NPC256567
0.8556	High Similarity	NPC253115
0.8556	High Similarity	NPC304899
0.8554	High Similarity	NPC50964
0.8554	High Similarity	NPC218616
0.8554	High Similarity	NPC201852
0.8554	High Similarity	NPC296701
0.8537	High Similarity	NPC13554
0.8523	High Similarity	NPC41554
0.8523	High Similarity	NPC97404
0.8519	High Similarity	NPC302041
0.8519	High Similarity	NPC85346
0.8519	High Similarity	NPC472502
0.8519	High Similarity	NPC475
0.8519	High Similarity	NPC275910
0.8519	High Similarity	NPC65897
0.8519	High Similarity	NPC472499
0.8519	High Similarity	NPC472500
0.85	High Similarity	NPC113733
0.85	High Similarity	NPC134330
0.85	High Similarity	NPC321381
0.85	High Similarity	NPC96319
0.85	High Similarity	NPC189883
0.85	High Similarity	NPC321016
0.85	High Similarity	NPC240604
0.85	High Similarity	NPC129165
0.85	High Similarity	NPC107059
0.85	High Similarity	NPC300324
0.8481	Intermediate Similarity	NPC308440
0.8481	Intermediate Similarity	NPC472503
0.8471	Intermediate Similarity	NPC470360
0.8462	Intermediate Similarity	NPC477226
0.8462	Intermediate Similarity	NPC190554
0.8452	Intermediate Similarity	NPC134481
0.8452	Intermediate Similarity	NPC470558
0.8452	Intermediate Similarity	NPC82623
0.8434	Intermediate Similarity	NPC476646
0.8434	Intermediate Similarity	NPC209620
0.8434	Intermediate Similarity	NPC23852
0.8434	Intermediate Similarity	NPC157655
0.8434	Intermediate Similarity	NPC474531
0.8415	Intermediate Similarity	NPC476316
0.8409	Intermediate Similarity	NPC295668
0.8409	Intermediate Similarity	NPC329596
0.8409	Intermediate Similarity	NPC11216
0.8409	Intermediate Similarity	NPC80561
0.8409	Intermediate Similarity	NPC291484
0.8409	Intermediate Similarity	NPC204188
0.8409	Intermediate Similarity	NPC3345
0.8409	Intermediate Similarity	NPC107189
0.8395	Intermediate Similarity	NPC198968
0.8395	Intermediate Similarity	NPC214570
0.8395	Intermediate Similarity	NPC202540
0.8395	Intermediate Similarity	NPC155986
0.8395	Intermediate Similarity	NPC138502
0.8395	Intermediate Similarity	NPC318495
0.8391	Intermediate Similarity	NPC474668
0.8391	Intermediate Similarity	NPC212596
0.8391	Intermediate Similarity	NPC4574
0.8391	Intermediate Similarity	NPC475605
0.8391	Intermediate Similarity	NPC471952
0.8391	Intermediate Similarity	NPC67872
0.8391	Intermediate Similarity	NPC133588
0.8375	Intermediate Similarity	NPC257347
0.8375	Intermediate Similarity	NPC230301
0.8375	Intermediate Similarity	NPC304309
0.8375	Intermediate Similarity	NPC291503
0.8375	Intermediate Similarity	NPC288035
0.8375	Intermediate Similarity	NPC162742
0.8375	Intermediate Similarity	NPC22105
0.8375	Intermediate Similarity	NPC285893
0.8375	Intermediate Similarity	NPC136188
0.8375	Intermediate Similarity	NPC134847
0.8375	Intermediate Similarity	NPC141071
0.8375	Intermediate Similarity	NPC3403
0.8375	Intermediate Similarity	NPC28657
0.8375	Intermediate Similarity	NPC471723
0.8372	Intermediate Similarity	NPC269058
0.8372	Intermediate Similarity	NPC94462
0.8372	Intermediate Similarity	NPC71520
0.8353	Intermediate Similarity	NPC469878
0.8353	Intermediate Similarity	NPC478102
0.8353	Intermediate Similarity	NPC205845
0.8352	Intermediate Similarity	NPC471903
0.8333	Intermediate Similarity	NPC63588
0.8333	Intermediate Similarity	NPC49964
0.8333	Intermediate Similarity	NPC101462
0.8333	Intermediate Similarity	NPC20853
0.8333	Intermediate Similarity	NPC30166
0.8333	Intermediate Similarity	NPC111015
0.8333	Intermediate Similarity	NPC232925
0.8333	Intermediate Similarity	NPC251201
0.8315	Intermediate Similarity	NPC275671
0.8313	Intermediate Similarity	NPC241290
0.8313	Intermediate Similarity	NPC475679
0.8313	Intermediate Similarity	NPC236112
0.8313	Intermediate Similarity	NPC234193
0.8313	Intermediate Similarity	NPC287749
0.8313	Intermediate Similarity	NPC164840
0.8313	Intermediate Similarity	NPC96362
0.8313	Intermediate Similarity	NPC209944
0.8295	Intermediate Similarity	NPC101886
0.8295	Intermediate Similarity	NPC470361
0.8293	Intermediate Similarity	NPC473943
0.8293	Intermediate Similarity	NPC31828
0.8293	Intermediate Similarity	NPC301707
0.8293	Intermediate Similarity	NPC76931
0.8293	Intermediate Similarity	NPC42853
0.8293	Intermediate Similarity	NPC307965
0.8293	Intermediate Similarity	NPC312328
0.8293	Intermediate Similarity	NPC477514
0.8293	Intermediate Similarity	NPC474216
0.8293	Intermediate Similarity	NPC18603
0.8293	Intermediate Similarity	NPC11908
0.828	Intermediate Similarity	NPC15390
0.828	Intermediate Similarity	NPC208358
0.8276	Intermediate Similarity	NPC304083
0.8276	Intermediate Similarity	NPC475313
0.8272	Intermediate Similarity	NPC14112
0.8272	Intermediate Similarity	NPC202642
0.8272	Intermediate Similarity	NPC470362
0.8272	Intermediate Similarity	NPC86305
0.8272	Intermediate Similarity	NPC46160
0.8272	Intermediate Similarity	NPC38141
0.8272	Intermediate Similarity	NPC73875
0.8261	Intermediate Similarity	NPC475032
0.8261	Intermediate Similarity	NPC475033
0.8256	Intermediate Similarity	NPC474189
0.8256	Intermediate Similarity	NPC22133
0.8256	Intermediate Similarity	NPC474349
0.825	Intermediate Similarity	NPC243342
0.825	Intermediate Similarity	NPC477138
0.8235	Intermediate Similarity	NPC216420
0.8235	Intermediate Similarity	NPC85095
0.8235	Intermediate Similarity	NPC211135
0.8228	Intermediate Similarity	NPC111234
0.8222	Intermediate Similarity	NPC98193
0.8214	Intermediate Similarity	NPC47761

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 NPC127606 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1679
0.2-0.3	4405
0.3-0.4	2066
0.4-0.5	391
0.5-0.6	171
0.6-0.7	183
0.7-0.8	89
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7525	Registered
0.85	High Similarity	NPD3701	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7339	Approved
0.8375	Intermediate Similarity	NPD6942	Approved
0.8068	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4785	Approved
0.8025	Intermediate Similarity	NPD4784	Approved
0.7805	Intermediate Similarity	NPD6924	Approved
0.7805	Intermediate Similarity	NPD6926	Approved
0.7778	Intermediate Similarity	NPD7150	Approved
0.7778	Intermediate Similarity	NPD7151	Approved
0.7778	Intermediate Similarity	NPD7152	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.7765	Intermediate Similarity	NPD7645	Phase 2
0.7765	Intermediate Similarity	NPD6929	Approved
0.7738	Intermediate Similarity	NPD6932	Approved
0.7727	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6931	Approved
0.7674	Intermediate Similarity	NPD4748	Discontinued
0.7674	Intermediate Similarity	NPD6930	Phase 2
0.7654	Intermediate Similarity	NPD7144	Approved
0.7654	Intermediate Similarity	NPD7143	Approved
0.7647	Intermediate Similarity	NPD7145	Approved
0.7634	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD6933	Approved
0.7614	Intermediate Similarity	NPD6695	Phase 3
0.7604	Intermediate Similarity	NPD7638	Approved
0.7531	Intermediate Similarity	NPD6922	Approved
0.7531	Intermediate Similarity	NPD6923	Approved
0.7529	Intermediate Similarity	NPD6925	Approved
0.7529	Intermediate Similarity	NPD5776	Phase 2
0.7527	Intermediate Similarity	NPD6079	Approved
0.7526	Intermediate Similarity	NPD7640	Approved
0.7526	Intermediate Similarity	NPD7639	Approved
0.7526	Intermediate Similarity	NPD4696	Approved
0.7526	Intermediate Similarity	NPD5286	Approved
0.7526	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD7509	Discontinued
0.7471	Intermediate Similarity	NPD7514	Phase 3
0.7449	Intermediate Similarity	NPD5223	Approved
0.7386	Intermediate Similarity	NPD6902	Approved
0.7374	Intermediate Similarity	NPD5225	Approved
0.7374	Intermediate Similarity	NPD5226	Approved
0.7374	Intermediate Similarity	NPD5224	Approved
0.7374	Intermediate Similarity	NPD4633	Approved
0.7374	Intermediate Similarity	NPD5211	Phase 2
0.7363	Intermediate Similarity	NPD3618	Phase 1
0.7356	Intermediate Similarity	NPD6683	Phase 2
0.7356	Intermediate Similarity	NPD4195	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7333	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3666	Approved
0.7317	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5175	Approved
0.73	Intermediate Similarity	NPD5174	Approved
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD5275	Approved
0.7283	Intermediate Similarity	NPD7524	Approved
0.7283	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD7332	Phase 2
0.7263	Intermediate Similarity	NPD6399	Phase 3
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6893	Approved
0.7229	Intermediate Similarity	NPD4787	Phase 1
0.7228	Intermediate Similarity	NPD5141	Approved
0.7216	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5221	Approved
0.7216	Intermediate Similarity	NPD5222	Approved
0.7212	Intermediate Similarity	NPD4634	Approved
0.7184	Intermediate Similarity	NPD6881	Approved
0.7184	Intermediate Similarity	NPD6899	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD5173	Approved
0.7129	Intermediate Similarity	NPD4754	Approved
0.7128	Intermediate Similarity	NPD4753	Phase 2
0.7087	Intermediate Similarity	NPD5697	Approved
0.7079	Intermediate Similarity	NPD6928	Phase 2
0.7048	Intermediate Similarity	NPD7290	Approved
0.7048	Intermediate Similarity	NPD7102	Approved
0.7048	Intermediate Similarity	NPD6883	Approved
0.7045	Intermediate Similarity	NPD6697	Approved
0.7045	Intermediate Similarity	NPD6118	Approved
0.7045	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6114	Approved
0.7045	Intermediate Similarity	NPD6115	Approved
0.7041	Intermediate Similarity	NPD4697	Phase 3
0.7033	Intermediate Similarity	NPD4788	Approved
0.7019	Intermediate Similarity	NPD4729	Approved
0.7019	Intermediate Similarity	NPD4730	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD6898	Phase 1
0.699	Remote Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD4767	Approved
0.6981	Remote Similarity	NPD6617	Approved
0.6981	Remote Similarity	NPD6847	Approved
0.6981	Remote Similarity	NPD8130	Phase 1
0.6981	Remote Similarity	NPD6650	Approved
0.6981	Remote Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD6649	Approved
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD7087	Discontinued
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD3668	Phase 3
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6932	Remote Similarity	NPD6116	Phase 1
0.6923	Remote Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD4221	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6916	Remote Similarity	NPD8297	Approved
0.6916	Remote Similarity	NPD6882	Approved
0.6909	Remote Similarity	NPD7328	Approved
0.6909	Remote Similarity	NPD7327	Approved
0.6897	Remote Similarity	NPD8264	Approved
0.6887	Remote Similarity	NPD5250	Approved
0.6887	Remote Similarity	NPD5135	Approved
0.6887	Remote Similarity	NPD5169	Approved
0.6887	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD5249	Phase 3
0.6887	Remote Similarity	NPD5248	Approved
0.6887	Remote Similarity	NPD5251	Approved
0.6882	Remote Similarity	NPD5329	Approved
0.6875	Remote Similarity	NPD8033	Approved
0.6863	Remote Similarity	NPD7632	Discontinued
0.6857	Remote Similarity	NPD5128	Approved
0.6847	Remote Similarity	NPD7516	Approved
0.6827	Remote Similarity	NPD6008	Approved
0.6822	Remote Similarity	NPD5127	Approved
0.6822	Remote Similarity	NPD5215	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5216	Approved
0.6822	Remote Similarity	NPD5217	Approved
0.6818	Remote Similarity	NPD6009	Approved
0.6818	Remote Similarity	NPD6117	Approved
0.6804	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6786	Remote Similarity	NPD8294	Approved
0.6786	Remote Similarity	NPD8377	Approved
0.6786	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD4197	Approved
0.6771	Remote Similarity	NPD6051	Approved
0.6762	Remote Similarity	NPD6412	Phase 2
0.6744	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5290	Discontinued
0.6726	Remote Similarity	NPD8379	Approved
0.6726	Remote Similarity	NPD8296	Approved
0.6726	Remote Similarity	NPD8380	Approved
0.6726	Remote Similarity	NPD8335	Approved
0.6726	Remote Similarity	NPD8378	Approved
0.6705	Remote Similarity	NPD3703	Phase 2
0.6701	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6637	Remote Similarity	NPD6059	Approved
0.6637	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD5167	Approved
0.6634	Remote Similarity	NPD7902	Approved
0.6633	Remote Similarity	NPD5281	Approved
0.6633	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD4689	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD5690	Phase 2
0.6632	Remote Similarity	NPD5279	Phase 3
0.6632	Remote Similarity	NPD5205	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6628	Remote Similarity	NPD4245	Approved
0.6628	Remote Similarity	NPD4244	Approved
0.6609	Remote Similarity	NPD7604	Phase 2
0.6607	Remote Similarity	NPD6335	Approved
0.6591	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6016	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