NPASS Compound

Structure

NPC473555 OpenBabel07101719142D 36 40 0 0 1 0 0 0 0 0999 V2000 -9.1664 4.4680 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1883 4.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 0 0 0 0 0 0 0 0 0 0 -7.8793 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 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 -6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 3 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 30 1 0 0 0 0 16 2 1 6 0 0 0 16 26 1 0 0 0 0 16 34 1 0 0 0 0 17 31 2 0 0 0 0 17 35 1 0 0 0 0 18 28 1 6 0 0 0 19 29 1 6 0 0 0 20 36 1 6 0 0 0 21 8 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 28 1 6 0 0 0 23 29 1 6 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 6 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 26 35 1 6 0 0 0 27 34 1 0 0 0 0 27 36 1 1 0 0 0 28 4 1 6 0 0 0 29 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.32
Volume:	523.616
LogP:	4.138
LogD:	4.158
LogS:	-4.136
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	5.061
Fsp3:	0.897
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	3.429076969041489e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.828
Human Intestinal Absorption (HIA):	0.292
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	89.3611831665039%
Volume Distribution (VD):	1.478
Pgp-substrate:	3.9153759479522705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.555
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	2.059
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.453
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.732
Skin Sensitization:	0.96
Carcinogencity:	0.25
Eye Corrosion:	0.087
Eye Irritation:	0.504
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473555

Natural Product ID:	NPC473555
*Common Name:**	Stereonsteroid C
IUPAC Name:	[(2S,3S,4S,5S,6R)-6-[[(3S,5S,8S,9S,10R,13R,14S,17R)-17-ethenyl-10-(hydroxymethyl)-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:	Stereonsteroid C
Standard InCHIKey:	INLRWOURCDBPMH-KFHYCKKOSA-N
Standard InCHI:	InChI=1S/C29H46O7/c1-5-18-7-9-22-21-8-6-19-14-20(10-13-29(19,15-30)23(21)11-12-28(18,22)4)36-27-25(33)24(32)26(16(2)34-27)35-17(3)31/h5,16,18-27,30,32-33H,1,6-15H2,2-4H3/t16-,18-,19-,20-,21-,22-,23-,24-,25-,26+,27-,28+,29+/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4CCC5C=C)C)CO)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445484
PubChem CID:	11641945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33076	stereonephthya crystalliana	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16441077]

☑ 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	1
IC50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[486898]
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.1	ug.mL-1	PMID[486898]

☑ 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 NPC473555 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	205
0.1-0.2	1878
0.2-0.3	6497
0.3-0.4	13815
0.4-0.5	8252
0.5-0.6	5013
0.6-0.7	4108
0.7-0.8	2492
0.8-0.85	359
0.85-0.9	69
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471770
1.0	High Similarity	NPC278939
0.989	High Similarity	NPC157739
0.9783	High Similarity	NPC317019
0.9444	High Similarity	NPC48463
0.9167	High Similarity	NPC154452
0.9091	High Similarity	NPC230888
0.9082	High Similarity	NPC473199
0.9062	High Similarity	NPC21064
0.9062	High Similarity	NPC121072
0.899	High Similarity	NPC234160
0.89	High Similarity	NPC472988
0.89	High Similarity	NPC38217
0.8889	High Similarity	NPC165405
0.8854	High Similarity	NPC234287
0.8854	High Similarity	NPC280825
0.8842	High Similarity	NPC472989
0.8812	High Similarity	NPC154085
0.8812	High Similarity	NPC296761
0.8812	High Similarity	NPC51925
0.8812	High Similarity	NPC125361
0.8812	High Similarity	NPC43976
0.8776	High Similarity	NPC94919
0.8763	High Similarity	NPC7341
0.8763	High Similarity	NPC473200
0.8713	High Similarity	NPC88744
0.8673	High Similarity	NPC47566
0.8673	High Similarity	NPC309425
0.8673	High Similarity	NPC88000
0.8673	High Similarity	NPC4831
0.8673	High Similarity	NPC160734
0.8673	High Similarity	NPC129372
0.8673	High Similarity	NPC472023
0.866	High Similarity	NPC158088
0.8646	High Similarity	NPC207617
0.8641	High Similarity	NPC65167
0.8641	High Similarity	NPC114188
0.8632	High Similarity	NPC211238
0.8627	High Similarity	NPC91583
0.8627	High Similarity	NPC473844
0.8627	High Similarity	NPC240125
0.8627	High Similarity	NPC51947
0.8614	High Similarity	NPC470169
0.8614	High Similarity	NPC470170
0.86	High Similarity	NPC312774
0.86	High Similarity	NPC85593
0.86	High Similarity	NPC475365
0.86	High Similarity	NPC31430
0.8586	High Similarity	NPC312553
0.8586	High Similarity	NPC136816
0.8586	High Similarity	NPC159036
0.8586	High Similarity	NPC288694
0.8571	High Similarity	NPC282669
0.8557	High Similarity	NPC243728
0.8557	High Similarity	NPC76486
0.8557	High Similarity	NPC473890
0.8529	High Similarity	NPC295389
0.8529	High Similarity	NPC295980
0.8526	High Similarity	NPC474835
0.85	High Similarity	NPC8039
0.85	High Similarity	NPC473198
0.85	High Similarity	NPC157659
0.85	High Similarity	NPC211879
0.85	High Similarity	NPC120123
0.85	High Similarity	NPC31907
0.85	High Similarity	NPC245280
0.85	High Similarity	NPC189852
0.85	High Similarity	NPC155010
0.85	High Similarity	NPC16573
0.85	High Similarity	NPC213190
0.85	High Similarity	NPC473020
0.85	High Similarity	NPC114874
0.85	High Similarity	NPC286969
0.85	High Similarity	NPC472252
0.85	High Similarity	NPC131479
0.85	High Similarity	NPC16520
0.8495	Intermediate Similarity	NPC263079
0.8485	Intermediate Similarity	NPC267510
0.8485	Intermediate Similarity	NPC470054
0.8485	Intermediate Similarity	NPC31346
0.8476	Intermediate Similarity	NPC144068
0.8469	Intermediate Similarity	NPC469725
0.8469	Intermediate Similarity	NPC477928
0.8462	Intermediate Similarity	NPC272242
0.8462	Intermediate Similarity	NPC285410
0.8462	Intermediate Similarity	NPC263827
0.8462	Intermediate Similarity	NPC250481
0.8462	Intermediate Similarity	NPC1876
0.8462	Intermediate Similarity	NPC240734
0.8462	Intermediate Similarity	NPC275668
0.8462	Intermediate Similarity	NPC91838
0.8462	Intermediate Similarity	NPC11035
0.8462	Intermediate Similarity	NPC204392
0.8438	Intermediate Similarity	NPC151214
0.8438	Intermediate Similarity	NPC191915
0.8438	Intermediate Similarity	NPC305160
0.8431	Intermediate Similarity	NPC470166
0.8431	Intermediate Similarity	NPC287269
0.8421	Intermediate Similarity	NPC219516
0.8416	Intermediate Similarity	NPC470060
0.8416	Intermediate Similarity	NPC470061
0.8416	Intermediate Similarity	NPC165033
0.8416	Intermediate Similarity	NPC273879
0.8416	Intermediate Similarity	NPC470058
0.8416	Intermediate Similarity	NPC470059
0.8416	Intermediate Similarity	NPC173583
0.8416	Intermediate Similarity	NPC470064
0.8416	Intermediate Similarity	NPC470057
0.8416	Intermediate Similarity	NPC470062
0.8416	Intermediate Similarity	NPC470043
0.84	Intermediate Similarity	NPC31085
0.84	Intermediate Similarity	NPC272015
0.84	Intermediate Similarity	NPC470053
0.84	Intermediate Similarity	NPC177701
0.8396	Intermediate Similarity	NPC471633
0.8396	Intermediate Similarity	NPC69576
0.8396	Intermediate Similarity	NPC84949
0.8396	Intermediate Similarity	NPC31354
0.8384	Intermediate Similarity	NPC471247
0.8384	Intermediate Similarity	NPC91497
0.8381	Intermediate Similarity	NPC243572
0.8381	Intermediate Similarity	NPC470543
0.837	Intermediate Similarity	NPC290612
0.8365	Intermediate Similarity	NPC129340
0.8351	Intermediate Similarity	NPC57964
0.8351	Intermediate Similarity	NPC275310
0.8351	Intermediate Similarity	NPC94582
0.8351	Intermediate Similarity	NPC286612
0.8351	Intermediate Similarity	NPC230347
0.835	Intermediate Similarity	NPC472897
0.835	Intermediate Similarity	NPC472896
0.835	Intermediate Similarity	NPC224414
0.8333	Intermediate Similarity	NPC470055
0.8333	Intermediate Similarity	NPC160816
0.8333	Intermediate Similarity	NPC470056
0.8333	Intermediate Similarity	NPC208477
0.8333	Intermediate Similarity	NPC194842
0.8333	Intermediate Similarity	NPC472899
0.8333	Intermediate Similarity	NPC208594
0.8333	Intermediate Similarity	NPC269627
0.8333	Intermediate Similarity	NPC69737
0.8333	Intermediate Similarity	NPC127801
0.8333	Intermediate Similarity	NPC152584
0.8333	Intermediate Similarity	NPC472900
0.8333	Intermediate Similarity	NPC472898
0.8318	Intermediate Similarity	NPC99620
0.8318	Intermediate Similarity	NPC5311
0.8318	Intermediate Similarity	NPC310341
0.8318	Intermediate Similarity	NPC193382
0.8318	Intermediate Similarity	NPC199428
0.8317	Intermediate Similarity	NPC471467
0.8316	Intermediate Similarity	NPC474249
0.8316	Intermediate Similarity	NPC471370
0.8316	Intermediate Similarity	NPC261990
0.8316	Intermediate Similarity	NPC471371
0.8302	Intermediate Similarity	NPC73986
0.8302	Intermediate Similarity	NPC146563
0.8302	Intermediate Similarity	NPC102619
0.83	Intermediate Similarity	NPC144486
0.83	Intermediate Similarity	NPC21568
0.83	Intermediate Similarity	NPC470434
0.83	Intermediate Similarity	NPC285231
0.8286	Intermediate Similarity	NPC470748
0.8283	Intermediate Similarity	NPC470068
0.8283	Intermediate Similarity	NPC474092
0.8283	Intermediate Similarity	NPC216260
0.8283	Intermediate Similarity	NPC5358
0.828	Intermediate Similarity	NPC471369
0.8269	Intermediate Similarity	NPC473570
0.8269	Intermediate Similarity	NPC265655
0.8269	Intermediate Similarity	NPC8431
0.8265	Intermediate Similarity	NPC296936
0.8265	Intermediate Similarity	NPC237071
0.8265	Intermediate Similarity	NPC238796
0.8265	Intermediate Similarity	NPC252056
0.8265	Intermediate Similarity	NPC471903
0.8265	Intermediate Similarity	NPC203434
0.8261	Intermediate Similarity	NPC299963
0.8252	Intermediate Similarity	NPC231340
0.8252	Intermediate Similarity	NPC181467
0.8252	Intermediate Similarity	NPC473469
0.8252	Intermediate Similarity	NPC63368
0.8252	Intermediate Similarity	NPC208650
0.8252	Intermediate Similarity	NPC14946
0.8247	Intermediate Similarity	NPC96736
0.8247	Intermediate Similarity	NPC178949
0.8241	Intermediate Similarity	NPC84987
0.8241	Intermediate Similarity	NPC99728
0.8241	Intermediate Similarity	NPC50305
0.8241	Intermediate Similarity	NPC157376
0.8241	Intermediate Similarity	NPC243196
0.8241	Intermediate Similarity	NPC471355
0.8241	Intermediate Similarity	NPC474418
0.8241	Intermediate Similarity	NPC93883
0.8241	Intermediate Similarity	NPC473852
0.8241	Intermediate Similarity	NPC471354
0.8241	Intermediate Similarity	NPC244402
0.8241	Intermediate Similarity	NPC471351
0.8241	Intermediate Similarity	NPC152615
0.8241	Intermediate Similarity	NPC471353

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 NPC473555 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	2248
0.2-0.3	4169
0.3-0.4	1654
0.4-0.5	442
0.5-0.6	283
0.6-0.7	147
0.7-0.8	24
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8165	Intermediate Similarity	NPD7328	Approved
0.8165	Intermediate Similarity	NPD7327	Approved
0.8131	Intermediate Similarity	NPD8133	Approved
0.8091	Intermediate Similarity	NPD7516	Approved
0.8018	Intermediate Similarity	NPD8377	Approved
0.8018	Intermediate Similarity	NPD8294	Approved
0.7946	Intermediate Similarity	NPD8033	Approved
0.7946	Intermediate Similarity	NPD8296	Approved
0.7946	Intermediate Similarity	NPD8335	Approved
0.7946	Intermediate Similarity	NPD8378	Approved
0.7946	Intermediate Similarity	NPD8380	Approved
0.7946	Intermediate Similarity	NPD8379	Approved
0.7905	Intermediate Similarity	NPD6412	Phase 2
0.7788	Intermediate Similarity	NPD7503	Approved
0.7778	Intermediate Similarity	NPD8171	Discontinued
0.7672	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD6686	Approved
0.7479	Intermediate Similarity	NPD7319	Approved
0.7447	Intermediate Similarity	NPD6928	Phase 2
0.7431	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7736	Approved
0.7383	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD8035	Phase 2
0.7327	Intermediate Similarity	NPD8034	Phase 2
0.7245	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7638	Approved
0.7203	Intermediate Similarity	NPD8328	Phase 3
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.713	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6370	Approved
0.7083	Intermediate Similarity	NPD7525	Registered
0.7043	Intermediate Similarity	NPD6940	Discontinued
0.7027	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD7492	Approved
0.6983	Remote Similarity	NPD6009	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6942	Remote Similarity	NPD6616	Approved
0.693	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6885	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD6118	Approved
0.6875	Remote Similarity	NPD6114	Approved
0.6875	Remote Similarity	NPD6697	Approved
0.6875	Remote Similarity	NPD6115	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.6771	Remote Similarity	NPD6116	Phase 1
0.6765	Remote Similarity	NPD7524	Approved
0.675	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD6015	Approved
0.6739	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6899	Approved
0.6726	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD7115	Discovery
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD6067	Discontinued
0.6637	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7645	Phase 2
0.6632	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7290	Approved
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.6579	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6562	Remote Similarity	NPD6942	Approved
0.6562	Remote Similarity	NPD7339	Approved
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6847	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3669	Approved
0.6535	Remote Similarity	NPD6695	Phase 3
0.6522	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6083	Phase 2
0.6514	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD7515	Phase 2
0.6504	Remote Similarity	NPD7604	Phase 2
0.6491	Remote Similarity	NPD5701	Approved
0.6484	Remote Similarity	NPD8449	Approved
0.6481	Remote Similarity	NPD7991	Discontinued
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.6475	Remote Similarity	NPD8515	Approved
0.6471	Remote Similarity	NPD7625	Phase 1
0.6471	Remote Similarity	NPD4786	Approved
0.6458	Remote Similarity	NPD1810	Approved
0.6458	Remote Similarity	NPD1811	Approved
0.6455	Remote Similarity	NPD4225	Approved
0.6435	Remote Similarity	NPD6011	Approved
0.6434	Remote Similarity	NPD8450	Suspended
0.64	Remote Similarity	NPD6336	Discontinued
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6079	Approved
0.6341	Remote Similarity	NPD6921	Approved
0.6339	Remote Similarity	NPD5344	Discontinued
0.6327	Remote Similarity	NPD6933	Approved
0.6327	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5328	Approved
0.6321	Remote Similarity	NPD6051	Approved
0.6316	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6929	Approved
0.6299	Remote Similarity	NPD6033	Approved
0.6286	Remote Similarity	NPD7750	Discontinued
0.6275	Remote Similarity	NPD3667	Approved
0.6271	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6932	Approved
0.6261	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7900	Approved
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6931	Approved
0.6238	Remote Similarity	NPD6930	Phase 2
0.6226	Remote Similarity	NPD5737	Approved
0.6226	Remote Similarity	NPD6672	Approved
0.6216	Remote Similarity	NPD4755	Approved
0.6214	Remote Similarity	NPD4788	Approved
0.6204	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD7145	Approved
0.619	Remote Similarity	NPD7146	Approved
0.619	Remote Similarity	NPD5330	Approved
0.619	Remote Similarity	NPD7334	Approved
0.619	Remote Similarity	NPD6409	Approved
0.619	Remote Similarity	NPD3618	Phase 1
0.619	Remote Similarity	NPD7521	Approved
0.619	Remote Similarity	NPD6684	Approved
0.6182	Remote Similarity	NPD5695	Phase 3
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6161	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD8174	Phase 2
0.6147	Remote Similarity	NPD4202	Approved
0.6146	Remote Similarity	NPD2686	Approved
0.6146	Remote Similarity	NPD2687	Approved
0.6146	Remote Similarity	NPD2254	Approved
0.614	Remote Similarity	NPD5225	Approved
0.614	Remote Similarity	NPD5211	Phase 2
0.614	Remote Similarity	NPD4633	Approved
0.614	Remote Similarity	NPD5224	Approved
0.614	Remote Similarity	NPD5226	Approved
0.6132	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5221	Approved
0.6126	Remote Similarity	NPD5222	Approved
0.6126	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6926	Approved
0.6122	Remote Similarity	NPD6924	Approved
0.6106	Remote Similarity	NPD4700	Approved
0.61	Remote Similarity	NPD5776	Phase 2
0.61	Remote Similarity	NPD6925	Approved
0.6098	Remote Similarity	NPD6335	Approved
0.6087	Remote Similarity	NPD5174	Approved
0.6087	Remote Similarity	NPD5175	Approved
0.6082	Remote Similarity	NPD7151	Approved
0.6082	Remote Similarity	NPD7152	Approved
0.6082	Remote Similarity	NPD7150	Approved
0.6078	Remote Similarity	NPD7514	Phase 3
0.6077	Remote Similarity	NPD5956	Approved
0.6075	Remote Similarity	NPD6903	Approved
0.6071	Remote Similarity	NPD5173	Approved
0.6066	Remote Similarity	NPD6274	Approved
0.6066	Remote Similarity	NPD6868	Approved
0.6061	Remote Similarity	NPD3703	Phase 2
0.6061	Remote Similarity	NPD3702	Approved
0.6055	Remote Similarity	NPD7087	Discontinued
0.6053	Remote Similarity	NPD5223	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5141	Approved
0.6019	Remote Similarity	NPD1779	Approved
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD1780	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