NPASS Compound

Structure

NPC12046 OpenBabel07101718312D 29 33 0 0 1 0 0 0 0 0999 V2000 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -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 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 22 1 0 0 0 0 2 22 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 16 24 1 1 0 0 0 16 25 1 0 0 0 0 17 23 1 1 0 0 0 17 24 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 1 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.28
Volume:	428.062
LogP:	4.489
LogD:	3.807
LogS:	-4.804
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	5.123
Fsp3:	0.88
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.746
MDCK Permeability:	2.9053546313662082e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.417
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.683
30% Bioavailability (F30%):	0.7

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	85.19570922851562%
Volume Distribution (VD):	1.825
Pgp-substrate:	21.54166030883789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.239
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.355
CYP3A4-inhibitor:	0.468
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	8.28
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.479
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.134
Carcinogencity:	0.063
Eye Corrosion:	0.037
Eye Irritation:	0.048
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC12046

Natural Product ID:	NPC12046
*Common Name:**	12-O-Deacetyl-12-Epi-Scalarin
IUPAC Name:	(1R,5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-1,13-dihydroxy-5b,8,8,11a,13a-pentamethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one
Synonyms:
Standard InCHIKey:	ATVQOEWPZTUPDT-PNXXKSHTSA-N
Standard InCHI:	InChI=1S/C25H38O4/c1-22(2)10-6-11-23(3)15(22)9-12-24(4)16-8-7-14-19(21(28)29-20(14)27)25(16,5)18(26)13-17(23)24/h7,15-19,21,26,28H,6,8-13H2,1-5H3/t15-,16-,17+,18+,19+,21+,23-,24-,25+/m0/s1
SMILES:	O[C@@H]1OC(=O)C2=CC[C@@H]3[C@]([C@@H]12)(C)[C@H](O)C[C@H]1[C@@]3(C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399743
PubChem CID:	10960421
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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	6

Activity Type	# Activity
Cell Line	4
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	IC50	=	75000.0	nM	PMID[520390]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.3	ug.mL-1	PMID[520391]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[520391]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14.8	ug.mL-1	PMID[520391]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	14.3	ug.mL-1	PMID[520391]
NPT27	Others	Unspecified		IC50	=	77200.0	nM	PMID[520390]

☑ 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 NPC12046 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	225
0.1-0.2	1334
0.2-0.3	3942
0.3-0.4	7272
0.4-0.5	12467
0.5-0.6	6913
0.6-0.7	5801
0.7-0.8	4130
0.8-0.85	543
0.85-0.9	57
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194951
0.9904	High Similarity	NPC157441
0.9612	High Similarity	NPC189075
0.9612	High Similarity	NPC275539
0.9519	High Similarity	NPC112457
0.9515	High Similarity	NPC110496
0.9223	High Similarity	NPC254202
0.9135	High Similarity	NPC222161
0.9057	High Similarity	NPC325054
0.9029	High Similarity	NPC63249
0.8942	High Similarity	NPC134077
0.8932	High Similarity	NPC477971
0.8932	High Similarity	NPC477972
0.8932	High Similarity	NPC219285
0.8932	High Similarity	NPC477968
0.8932	High Similarity	NPC228251
0.8932	High Similarity	NPC20113
0.8932	High Similarity	NPC161527
0.8919	High Similarity	NPC473968
0.8868	High Similarity	NPC469607
0.8857	High Similarity	NPC471208
0.8818	High Similarity	NPC25909
0.8796	High Similarity	NPC31522
0.8762	High Similarity	NPC165250
0.8761	High Similarity	NPC476529
0.8761	High Similarity	NPC475775
0.8727	High Similarity	NPC277769
0.8704	High Similarity	NPC300614
0.8704	High Similarity	NPC90946
0.8684	High Similarity	NPC109607
0.8684	High Similarity	NPC107338
0.8667	High Similarity	NPC471412
0.8654	High Similarity	NPC473154
0.8624	High Similarity	NPC476759
0.8596	High Similarity	NPC122971
0.8585	High Similarity	NPC469606
0.8585	High Similarity	NPC476769
0.8585	High Similarity	NPC273005
0.8585	High Similarity	NPC162973
0.8585	High Similarity	NPC31058
0.8584	High Similarity	NPC13713
0.8571	High Similarity	NPC476767
0.8571	High Similarity	NPC471413
0.8571	High Similarity	NPC47024
0.8559	High Similarity	NPC4573
0.8559	High Similarity	NPC269530
0.8559	High Similarity	NPC90952
0.8558	High Similarity	NPC257726
0.8558	High Similarity	NPC76266
0.8558	High Similarity	NPC224356
0.8558	High Similarity	NPC132753
0.8558	High Similarity	NPC121402
0.8558	High Similarity	NPC175351
0.8558	High Similarity	NPC204054
0.8558	High Similarity	NPC151681
0.8545	High Similarity	NPC472666
0.8544	High Similarity	NPC135224
0.8544	High Similarity	NPC477969
0.8532	High Similarity	NPC476765
0.8532	High Similarity	NPC469844
0.8519	High Similarity	NPC127609
0.8519	High Similarity	NPC478208
0.8519	High Similarity	NPC252296
0.8505	High Similarity	NPC478057
0.8505	High Similarity	NPC95899
0.8505	High Similarity	NPC282233
0.8505	High Similarity	NPC95585
0.8496	Intermediate Similarity	NPC471816
0.8487	Intermediate Similarity	NPC473620
0.8476	Intermediate Similarity	NPC23364
0.8476	Intermediate Similarity	NPC216478
0.8462	Intermediate Similarity	NPC8954
0.8462	Intermediate Similarity	NPC472363
0.8462	Intermediate Similarity	NPC472362
0.8462	Intermediate Similarity	NPC94905
0.8462	Intermediate Similarity	NPC154526
0.8455	Intermediate Similarity	NPC472534
0.8455	Intermediate Similarity	NPC143706
0.8447	Intermediate Similarity	NPC189513
0.8447	Intermediate Similarity	NPC250075
0.844	Intermediate Similarity	NPC184512
0.843	Intermediate Similarity	NPC478150
0.843	Intermediate Similarity	NPC478153
0.843	Intermediate Similarity	NPC478152
0.8421	Intermediate Similarity	NPC474483
0.8421	Intermediate Similarity	NPC134430
0.8411	Intermediate Similarity	NPC476081
0.8411	Intermediate Similarity	NPC238397
0.8411	Intermediate Similarity	NPC136289
0.8411	Intermediate Similarity	NPC471363
0.8407	Intermediate Similarity	NPC472274
0.8403	Intermediate Similarity	NPC42399
0.8403	Intermediate Similarity	NPC298841
0.8396	Intermediate Similarity	NPC471041
0.839	Intermediate Similarity	NPC470922
0.8381	Intermediate Similarity	NPC474343
0.8378	Intermediate Similarity	NPC476766
0.8378	Intermediate Similarity	NPC235014
0.8365	Intermediate Similarity	NPC183012
0.8365	Intermediate Similarity	NPC100892
0.8365	Intermediate Similarity	NPC477970
0.8364	Intermediate Similarity	NPC473483
0.8364	Intermediate Similarity	NPC476802
0.8364	Intermediate Similarity	NPC89171
0.8364	Intermediate Similarity	NPC469845
0.8362	Intermediate Similarity	NPC48692
0.8362	Intermediate Similarity	NPC470312
0.8361	Intermediate Similarity	NPC478151
0.835	Intermediate Similarity	NPC166346
0.8349	Intermediate Similarity	NPC218158
0.8349	Intermediate Similarity	NPC172867
0.8349	Intermediate Similarity	NPC102352
0.8348	Intermediate Similarity	NPC475913
0.8347	Intermediate Similarity	NPC475377
0.8347	Intermediate Similarity	NPC478065
0.8347	Intermediate Similarity	NPC172374
0.8347	Intermediate Similarity	NPC173435
0.8347	Intermediate Similarity	NPC45346
0.8347	Intermediate Similarity	NPC477197
0.8347	Intermediate Similarity	NPC478155
0.8347	Intermediate Similarity	NPC476074
0.8347	Intermediate Similarity	NPC478064
0.8347	Intermediate Similarity	NPC264566
0.8347	Intermediate Similarity	NPC301639
0.8347	Intermediate Similarity	NPC134914
0.8347	Intermediate Similarity	NPC25998
0.8347	Intermediate Similarity	NPC329993
0.8347	Intermediate Similarity	NPC262796
0.8347	Intermediate Similarity	NPC475167
0.8333	Intermediate Similarity	NPC36688
0.8333	Intermediate Similarity	NPC268954
0.8333	Intermediate Similarity	NPC471364
0.8333	Intermediate Similarity	NPC127933
0.8333	Intermediate Similarity	NPC45606
0.8333	Intermediate Similarity	NPC7613
0.8333	Intermediate Similarity	NPC134270
0.8333	Intermediate Similarity	NPC132395
0.8333	Intermediate Similarity	NPC471365
0.8333	Intermediate Similarity	NPC475889
0.8333	Intermediate Similarity	NPC44170
0.8333	Intermediate Similarity	NPC7644
0.8333	Intermediate Similarity	NPC220838
0.8319	Intermediate Similarity	NPC51978
0.8319	Intermediate Similarity	NPC264153
0.8318	Intermediate Similarity	NPC81530
0.8305	Intermediate Similarity	NPC469382
0.8305	Intermediate Similarity	NPC27363
0.8304	Intermediate Similarity	NPC201992
0.8304	Intermediate Similarity	NPC469655
0.8304	Intermediate Similarity	NPC474846
0.8304	Intermediate Similarity	NPC469656
0.8302	Intermediate Similarity	NPC58942
0.8302	Intermediate Similarity	NPC260149
0.8302	Intermediate Similarity	NPC478056
0.8291	Intermediate Similarity	NPC476204
0.8291	Intermediate Similarity	NPC202051
0.8291	Intermediate Similarity	NPC170084
0.8288	Intermediate Similarity	NPC478210
0.8288	Intermediate Similarity	NPC474243
0.8286	Intermediate Similarity	NPC29952
0.8279	Intermediate Similarity	NPC478154
0.8279	Intermediate Similarity	NPC471855
0.8276	Intermediate Similarity	NPC473636
0.8276	Intermediate Similarity	NPC77689
0.8276	Intermediate Similarity	NPC475041
0.8276	Intermediate Similarity	NPC477071
0.8276	Intermediate Similarity	NPC475834
0.8276	Intermediate Similarity	NPC470914
0.8276	Intermediate Similarity	NPC474179
0.8273	Intermediate Similarity	NPC475570
0.8273	Intermediate Similarity	NPC109376
0.8273	Intermediate Similarity	NPC230541
0.8273	Intermediate Similarity	NPC293512
0.8273	Intermediate Similarity	NPC144854
0.8273	Intermediate Similarity	NPC3316
0.8269	Intermediate Similarity	NPC57117
0.8264	Intermediate Similarity	NPC470913
0.8264	Intermediate Similarity	NPC477076
0.8264	Intermediate Similarity	NPC477077
0.8264	Intermediate Similarity	NPC473593
0.8264	Intermediate Similarity	NPC477079
0.8264	Intermediate Similarity	NPC477196
0.8261	Intermediate Similarity	NPC23046
0.8261	Intermediate Similarity	NPC284068
0.8261	Intermediate Similarity	NPC475809
0.8261	Intermediate Similarity	NPC473590
0.8257	Intermediate Similarity	NPC470321
0.8257	Intermediate Similarity	NPC476764
0.8257	Intermediate Similarity	NPC201880
0.8257	Intermediate Similarity	NPC264867
0.8257	Intermediate Similarity	NPC473207
0.8257	Intermediate Similarity	NPC81567
0.8257	Intermediate Similarity	NPC476763
0.8252	Intermediate Similarity	NPC233345
0.8252	Intermediate Similarity	NPC186363
0.825	Intermediate Similarity	NPC470780
0.8246	Intermediate Similarity	NPC469877
0.8246	Intermediate Similarity	NPC18547
0.8246	Intermediate Similarity	NPC475633
0.8246	Intermediate Similarity	NPC474906

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 NPC12046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1507
0.2-0.3	3548
0.3-0.4	2487
0.4-0.5	849
0.5-0.6	280
0.6-0.7	153
0.7-0.8	124
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8302	Intermediate Similarity	NPD7638	Approved
0.8224	Intermediate Similarity	NPD7640	Approved
0.8224	Intermediate Similarity	NPD7639	Approved
0.8198	Intermediate Similarity	NPD6686	Approved
0.8167	Intermediate Similarity	NPD7507	Approved
0.7967	Intermediate Similarity	NPD7319	Approved
0.7886	Intermediate Similarity	NPD7736	Approved
0.787	Intermediate Similarity	NPD7902	Approved
0.7851	Intermediate Similarity	NPD8328	Phase 3
0.7757	Intermediate Similarity	NPD7748	Approved
0.7736	Intermediate Similarity	NPD7515	Phase 2
0.7699	Intermediate Similarity	NPD6008	Approved
0.7647	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4225	Approved
0.7632	Intermediate Similarity	NPD6412	Phase 2
0.7623	Intermediate Similarity	NPD6370	Approved
0.7607	Intermediate Similarity	NPD6882	Approved
0.7593	Intermediate Similarity	NPD7900	Approved
0.7593	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD7632	Discontinued
0.7583	Intermediate Similarity	NPD7328	Approved
0.7583	Intermediate Similarity	NPD7327	Approved
0.7565	Intermediate Similarity	NPD6899	Approved
0.7565	Intermediate Similarity	NPD6881	Approved
0.7544	Intermediate Similarity	NPD5739	Approved
0.7544	Intermediate Similarity	NPD6675	Approved
0.7544	Intermediate Similarity	NPD6402	Approved
0.7544	Intermediate Similarity	NPD7128	Approved
0.7541	Intermediate Similarity	NPD8033	Approved
0.7541	Intermediate Similarity	NPD8517	Approved
0.7541	Intermediate Similarity	NPD8513	Phase 3
0.7541	Intermediate Similarity	NPD8515	Approved
0.7541	Intermediate Similarity	NPD8516	Approved
0.7521	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.7521	Intermediate Similarity	NPD6649	Approved
0.752	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD6373	Approved
0.7478	Intermediate Similarity	NPD5697	Approved
0.7459	Intermediate Similarity	NPD8294	Approved
0.7459	Intermediate Similarity	NPD8377	Approved
0.7459	Intermediate Similarity	NPD6054	Approved
0.744	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6883	Approved
0.7436	Intermediate Similarity	NPD7290	Approved
0.7436	Intermediate Similarity	NPD7102	Approved
0.7414	Intermediate Similarity	NPD7320	Approved
0.7414	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD6079	Approved
0.7398	Intermediate Similarity	NPD8296	Approved
0.7398	Intermediate Similarity	NPD8380	Approved
0.7398	Intermediate Similarity	NPD8379	Approved
0.7398	Intermediate Similarity	NPD8335	Approved
0.7398	Intermediate Similarity	NPD8378	Approved
0.7398	Intermediate Similarity	NPD7503	Approved
0.7395	Intermediate Similarity	NPD4632	Approved
0.7395	Intermediate Similarity	NPD8133	Approved
0.7383	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD7078	Approved
0.7373	Intermediate Similarity	NPD6617	Approved
0.7373	Intermediate Similarity	NPD6847	Approved
0.7373	Intermediate Similarity	NPD6869	Approved
0.7373	Intermediate Similarity	NPD8130	Phase 1
0.735	Intermediate Similarity	NPD6012	Approved
0.735	Intermediate Similarity	NPD6014	Approved
0.735	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.7328	Intermediate Similarity	NPD5701	Approved
0.7317	Intermediate Similarity	NPD6059	Approved
0.7311	Intermediate Similarity	NPD8297	Approved
0.7311	Intermediate Similarity	NPD6053	Discontinued
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7258	Intermediate Similarity	NPD6016	Approved
0.7258	Intermediate Similarity	NPD6015	Approved
0.7248	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD8034	Phase 2
0.7227	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5988	Approved
0.7196	Intermediate Similarity	NPD3573	Approved
0.7179	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD6067	Discontinued
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5211	Phase 2
0.712	Intermediate Similarity	NPD5983	Phase 2
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5285	Approved
0.7105	Intermediate Similarity	NPD5286	Approved
0.7105	Intermediate Similarity	NPD4696	Approved
0.708	Intermediate Similarity	NPD5173	Approved
0.708	Intermediate Similarity	NPD4755	Approved
0.7054	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5223	Approved
0.7031	Intermediate Similarity	NPD6336	Discontinued
0.7027	Intermediate Similarity	NPD5779	Approved
0.7027	Intermediate Similarity	NPD5778	Approved
0.7016	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5141	Approved
0.6992	Remote Similarity	NPD6274	Approved
0.6992	Remote Similarity	NPD6868	Approved
0.6984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5226	Approved
0.6983	Remote Similarity	NPD5225	Approved
0.6983	Remote Similarity	NPD4633	Approved
0.6983	Remote Similarity	NPD5224	Approved
0.696	Remote Similarity	NPD7101	Approved
0.696	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD7334	Approved
0.6944	Remote Similarity	NPD6684	Approved
0.6944	Remote Similarity	NPD6409	Approved
0.6944	Remote Similarity	NPD7521	Approved
0.6944	Remote Similarity	NPD5330	Approved
0.6944	Remote Similarity	NPD7146	Approved
0.6937	Remote Similarity	NPD6411	Approved
0.6935	Remote Similarity	NPD6317	Approved
0.693	Remote Similarity	NPD6084	Phase 2
0.693	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD6033	Approved
0.6916	Remote Similarity	NPD4786	Approved
0.6916	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7260	Phase 2
0.6887	Remote Similarity	NPD3667	Approved
0.688	Remote Similarity	NPD6313	Approved
0.688	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD4202	Approved
0.686	Remote Similarity	NPD4634	Approved
0.6847	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6698	Approved
0.6846	Remote Similarity	NPD8074	Phase 3
0.6818	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD5737	Approved
0.6803	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4754	Approved
0.6759	Remote Similarity	NPD3666	Approved
0.6759	Remote Similarity	NPD3133	Approved
0.6759	Remote Similarity	NPD3665	Phase 1
0.6757	Remote Similarity	NPD6101	Approved
0.6757	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5696	Approved
0.6721	Remote Similarity	NPD6371	Approved
0.6719	Remote Similarity	NPD6908	Approved
0.6719	Remote Similarity	NPD6909	Approved
0.6716	Remote Similarity	NPD6845	Suspended
0.6696	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6637	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5695	Phase 3
0.6604	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD5247	Approved
0.6585	Remote Similarity	NPD5249	Phase 3
0.6585	Remote Similarity	NPD5250	Approved
0.6585	Remote Similarity	NPD5251	Approved
0.6585	Remote Similarity	NPD5135	Approved
0.6585	Remote Similarity	NPD5169	Approved
0.6585	Remote Similarity	NPD5248	Approved
0.6585	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5168	Approved
0.6552	Remote Similarity	NPD7614	Phase 1
0.6542	Remote Similarity	NPD4695	Discontinued
0.6542	Remote Similarity	NPD7525	Registered
0.6532	Remote Similarity	NPD5216	Approved
0.6532	Remote Similarity	NPD5127	Approved
0.6532	Remote Similarity	NPD5215	Approved
0.6532	Remote Similarity	NPD5217	Approved
0.6525	Remote Similarity	NPD6648	Approved
0.6522	Remote Similarity	NPD6001	Approved
0.6509	Remote Similarity	NPD6697	Approved
0.6509	Remote Similarity	NPD6115	Approved
0.6509	Remote Similarity	NPD6118	Approved
0.6509	Remote Similarity	NPD6114	Approved
0.6491	Remote Similarity	NPD5284	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