NPASS Compound

Structure

NPC157441 OpenBabel07101719252D 30 34 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 -0.6994 -1.9680 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 23 1 0 0 0 0 2 23 1 0 0 0 0 6 29 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 1 0 0 0 17 25 1 1 0 0 0 17 26 1 0 0 0 0 18 24 1 1 0 0 0 18 25 1 0 0 0 0 19 26 1 1 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 26 1 1 0 0 0 21 28 2 0 0 0 0 21 30 1 0 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 24 3 1 1 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.29
Volume:	445.358
LogP:	5.254
LogD:	4.218
LogS:	-5.683
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	4.944
Fsp3:	0.885
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:	-4.759
MDCK Permeability:	2.928969479398802e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	91.60613250732422%
Volume Distribution (VD):	2.281
Pgp-substrate:	6.327249050140381%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.31
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.436
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	8.474
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.524
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.745
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.884
Carcinogencity:	0.025
Eye Corrosion:	0.756
Eye Irritation:	0.368
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: NPC157441

Natural Product ID:	NPC157441
*Common Name:**	12-O-Deacetyl-12-Epi-19-O-Methylscalarin
IUPAC Name:	(1R,5aS,5bR,7aS,11aS,11bR,13R,13aS,13bR)-13-hydroxy-1-methoxy-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:	SZCOSHPHASAUBT-WCGKCGFQSA-N
Standard InCHI:	InChI=1S/C26H40O4/c1-23(2)11-7-12-24(3)16(23)10-13-25(4)17-9-8-15-20(22(29-6)30-21(15)28)26(17,5)19(27)14-18(24)25/h8,16-20,22,27H,7,9-14H2,1-6H3/t16-,17-,18+,19+,20+,22+,24-,25-,26+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3CC=C4[C@H]([C@H](OC)OC4=O)[C@@]3(C)[C@@H](C[C@H]21)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251696
PubChem CID:	24178772
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	2

Activity Type	# Activity
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	=	24000.0	nM	PMID[515001]
NPT27	Others	Unspecified		IC50	=	48000.0	nM	PMID[515001]

☑ 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 NPC157441 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	228
0.1-0.2	1357
0.2-0.3	3999
0.3-0.4	7360
0.4-0.5	12195
0.5-0.6	7119
0.6-0.7	5791
0.7-0.8	4007
0.8-0.85	573
0.85-0.9	57
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9904	High Similarity	NPC194951
0.9904	High Similarity	NPC12046
0.9615	High Similarity	NPC112457
0.9519	High Similarity	NPC189075
0.9519	High Similarity	NPC275539
0.9423	High Similarity	NPC110496
0.9135	High Similarity	NPC254202
0.9048	High Similarity	NPC222161
0.9038	High Similarity	NPC134077
0.8972	High Similarity	NPC325054
0.8942	High Similarity	NPC63249
0.8846	High Similarity	NPC477972
0.8846	High Similarity	NPC20113
0.8846	High Similarity	NPC228251
0.8846	High Similarity	NPC477971
0.8846	High Similarity	NPC161527
0.8846	High Similarity	NPC219285
0.8846	High Similarity	NPC477968
0.8839	High Similarity	NPC473968
0.8785	High Similarity	NPC469607
0.8774	High Similarity	NPC471208
0.875	High Similarity	NPC473154
0.8739	High Similarity	NPC25909
0.8716	High Similarity	NPC476759
0.8716	High Similarity	NPC31522
0.8684	High Similarity	NPC475775
0.8684	High Similarity	NPC122971
0.8684	High Similarity	NPC476529
0.8679	High Similarity	NPC165250
0.8679	High Similarity	NPC476769
0.8654	High Similarity	NPC204054
0.8654	High Similarity	NPC257726
0.8649	High Similarity	NPC277769
0.8624	High Similarity	NPC300614
0.8624	High Similarity	NPC90946
0.8611	High Similarity	NPC127609
0.8611	High Similarity	NPC252296
0.8609	High Similarity	NPC109607
0.8609	High Similarity	NPC107338
0.8585	High Similarity	NPC471412
0.8584	High Similarity	NPC471816
0.8558	High Similarity	NPC94905
0.8558	High Similarity	NPC8954
0.8532	High Similarity	NPC184512
0.8512	High Similarity	NPC478152
0.8512	High Similarity	NPC478150
0.8512	High Similarity	NPC478153
0.8509	High Similarity	NPC474483
0.8509	High Similarity	NPC13713
0.8505	High Similarity	NPC273005
0.8505	High Similarity	NPC471363
0.8505	High Similarity	NPC238397
0.8505	High Similarity	NPC31058
0.8505	High Similarity	NPC162973
0.8505	High Similarity	NPC469606
0.8496	Intermediate Similarity	NPC472274
0.8491	Intermediate Similarity	NPC471413
0.8491	Intermediate Similarity	NPC47024
0.8491	Intermediate Similarity	NPC476767
0.8487	Intermediate Similarity	NPC298841
0.8487	Intermediate Similarity	NPC42399
0.8482	Intermediate Similarity	NPC90952
0.8482	Intermediate Similarity	NPC4573
0.8482	Intermediate Similarity	NPC269530
0.8476	Intermediate Similarity	NPC121402
0.8476	Intermediate Similarity	NPC151681
0.8476	Intermediate Similarity	NPC132753
0.8476	Intermediate Similarity	NPC224356
0.8476	Intermediate Similarity	NPC175351
0.8476	Intermediate Similarity	NPC76266
0.8468	Intermediate Similarity	NPC472666
0.8468	Intermediate Similarity	NPC476766
0.8462	Intermediate Similarity	NPC135224
0.8462	Intermediate Similarity	NPC100892
0.8462	Intermediate Similarity	NPC477970
0.8462	Intermediate Similarity	NPC477969
0.8455	Intermediate Similarity	NPC476765
0.8455	Intermediate Similarity	NPC469844
0.8448	Intermediate Similarity	NPC470312
0.8448	Intermediate Similarity	NPC48692
0.8443	Intermediate Similarity	NPC478151
0.844	Intermediate Similarity	NPC478208
0.844	Intermediate Similarity	NPC218158
0.844	Intermediate Similarity	NPC172867
0.843	Intermediate Similarity	NPC173435
0.843	Intermediate Similarity	NPC262796
0.843	Intermediate Similarity	NPC45346
0.843	Intermediate Similarity	NPC134914
0.843	Intermediate Similarity	NPC329993
0.843	Intermediate Similarity	NPC478155
0.843	Intermediate Similarity	NPC264566
0.843	Intermediate Similarity	NPC478064
0.843	Intermediate Similarity	NPC301639
0.843	Intermediate Similarity	NPC477197
0.843	Intermediate Similarity	NPC478065
0.843	Intermediate Similarity	NPC475167
0.843	Intermediate Similarity	NPC475377
0.843	Intermediate Similarity	NPC476074
0.843	Intermediate Similarity	NPC172374
0.843	Intermediate Similarity	NPC25998
0.8426	Intermediate Similarity	NPC132395
0.8426	Intermediate Similarity	NPC95585
0.8426	Intermediate Similarity	NPC475889
0.8426	Intermediate Similarity	NPC471364
0.8426	Intermediate Similarity	NPC134270
0.8426	Intermediate Similarity	NPC127933
0.8426	Intermediate Similarity	NPC95899
0.8426	Intermediate Similarity	NPC7644
0.8426	Intermediate Similarity	NPC282233
0.8426	Intermediate Similarity	NPC7613
0.8426	Intermediate Similarity	NPC471365
0.8426	Intermediate Similarity	NPC478057
0.8417	Intermediate Similarity	NPC45606
0.8417	Intermediate Similarity	NPC473620
0.8417	Intermediate Similarity	NPC220838
0.8407	Intermediate Similarity	NPC264153
0.8396	Intermediate Similarity	NPC23364
0.8396	Intermediate Similarity	NPC216478
0.839	Intermediate Similarity	NPC27363
0.8381	Intermediate Similarity	NPC472363
0.8381	Intermediate Similarity	NPC154526
0.8381	Intermediate Similarity	NPC472362
0.8378	Intermediate Similarity	NPC143706
0.8378	Intermediate Similarity	NPC472534
0.8376	Intermediate Similarity	NPC202051
0.8376	Intermediate Similarity	NPC476204
0.8376	Intermediate Similarity	NPC170084
0.8365	Intermediate Similarity	NPC250075
0.8365	Intermediate Similarity	NPC189513
0.8364	Intermediate Similarity	NPC293512
0.8364	Intermediate Similarity	NPC109376
0.8362	Intermediate Similarity	NPC474179
0.8362	Intermediate Similarity	NPC475834
0.8362	Intermediate Similarity	NPC477071
0.8362	Intermediate Similarity	NPC470914
0.8361	Intermediate Similarity	NPC471855
0.8361	Intermediate Similarity	NPC478154
0.8349	Intermediate Similarity	NPC476764
0.8349	Intermediate Similarity	NPC201880
0.8349	Intermediate Similarity	NPC476763
0.8349	Intermediate Similarity	NPC264867
0.8349	Intermediate Similarity	NPC470321
0.8349	Intermediate Similarity	NPC81567
0.8349	Intermediate Similarity	NPC473207
0.8348	Intermediate Similarity	NPC134430
0.8348	Intermediate Similarity	NPC23046
0.8347	Intermediate Similarity	NPC477077
0.8347	Intermediate Similarity	NPC477076
0.8347	Intermediate Similarity	NPC477079
0.8347	Intermediate Similarity	NPC477196
0.8347	Intermediate Similarity	NPC473593
0.8347	Intermediate Similarity	NPC470913
0.8333	Intermediate Similarity	NPC476081
0.8333	Intermediate Similarity	NPC475633
0.8333	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC470780
0.8319	Intermediate Similarity	NPC75856
0.8319	Intermediate Similarity	NPC470922
0.8319	Intermediate Similarity	NPC469379
0.8319	Intermediate Similarity	NPC222834
0.8319	Intermediate Similarity	NPC86346
0.8318	Intermediate Similarity	NPC471041
0.8305	Intermediate Similarity	NPC473231
0.8304	Intermediate Similarity	NPC235014
0.8304	Intermediate Similarity	NPC83005
0.8304	Intermediate Similarity	NPC119550
0.8302	Intermediate Similarity	NPC474343
0.8291	Intermediate Similarity	NPC476127
0.8291	Intermediate Similarity	NPC476150
0.8288	Intermediate Similarity	NPC469845
0.8288	Intermediate Similarity	NPC219900
0.8288	Intermediate Similarity	NPC470024
0.8288	Intermediate Similarity	NPC476802
0.8288	Intermediate Similarity	NPC89171
0.8288	Intermediate Similarity	NPC473483
0.8288	Intermediate Similarity	NPC177524
0.8288	Intermediate Similarity	NPC224660
0.8288	Intermediate Similarity	NPC392
0.8286	Intermediate Similarity	NPC183012
0.8279	Intermediate Similarity	NPC311178
0.8279	Intermediate Similarity	NPC300655
0.8279	Intermediate Similarity	NPC43589
0.8279	Intermediate Similarity	NPC222951
0.8276	Intermediate Similarity	NPC475913
0.8273	Intermediate Similarity	NPC102352
0.8273	Intermediate Similarity	NPC476760
0.8273	Intermediate Similarity	NPC476762
0.8273	Intermediate Similarity	NPC476761
0.8269	Intermediate Similarity	NPC166346
0.8264	Intermediate Similarity	NPC477193
0.8264	Intermediate Similarity	NPC311534
0.8264	Intermediate Similarity	NPC477194
0.8264	Intermediate Similarity	NPC477192
0.8264	Intermediate Similarity	NPC477191
0.8264	Intermediate Similarity	NPC477078
0.8264	Intermediate Similarity	NPC477075
0.8264	Intermediate Similarity	NPC475281
0.8264	Intermediate Similarity	NPC329923
0.8264	Intermediate Similarity	NPC245094
0.8261	Intermediate Similarity	NPC44170

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 NPC157441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1531
0.2-0.3	3574
0.3-0.4	2445
0.4-0.5	836
0.5-0.6	283
0.6-0.7	164
0.7-0.8	109
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
0.8288	Intermediate Similarity	NPD6686	Approved
0.825	Intermediate Similarity	NPD7507	Approved
0.8224	Intermediate Similarity	NPD7638	Approved
0.8148	Intermediate Similarity	NPD7640	Approved
0.8148	Intermediate Similarity	NPD7639	Approved
0.8049	Intermediate Similarity	NPD7319	Approved
0.7967	Intermediate Similarity	NPD7736	Approved
0.7934	Intermediate Similarity	NPD8328	Phase 3
0.7798	Intermediate Similarity	NPD7902	Approved
0.7731	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6412	Phase 2
0.7705	Intermediate Similarity	NPD6370	Approved
0.7692	Intermediate Similarity	NPD6882	Approved
0.7685	Intermediate Similarity	NPD7748	Approved
0.7667	Intermediate Similarity	NPD7327	Approved
0.7667	Intermediate Similarity	NPD7328	Approved
0.7664	Intermediate Similarity	NPD7515	Phase 2
0.7632	Intermediate Similarity	NPD6008	Approved
0.7623	Intermediate Similarity	NPD8513	Phase 3
0.7623	Intermediate Similarity	NPD8517	Approved
0.7623	Intermediate Similarity	NPD8516	Approved
0.7623	Intermediate Similarity	NPD8515	Approved
0.7623	Intermediate Similarity	NPD8033	Approved
0.7603	Intermediate Similarity	NPD7516	Approved
0.76	Intermediate Similarity	NPD8293	Discontinued
0.7586	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7583	Intermediate Similarity	NPD6009	Approved
0.7581	Intermediate Similarity	NPD7492	Approved
0.7568	Intermediate Similarity	NPD4225	Approved
0.7541	Intermediate Similarity	NPD6054	Approved
0.7541	Intermediate Similarity	NPD8377	Approved
0.7541	Intermediate Similarity	NPD8294	Approved
0.7523	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7900	Approved
0.7522	Intermediate Similarity	NPD7632	Discontinued
0.752	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.748	Intermediate Similarity	NPD8335	Approved
0.748	Intermediate Similarity	NPD7503	Approved
0.748	Intermediate Similarity	NPD8380	Approved
0.748	Intermediate Similarity	NPD8378	Approved
0.748	Intermediate Similarity	NPD8379	Approved
0.748	Intermediate Similarity	NPD8296	Approved
0.7479	Intermediate Similarity	NPD8133	Approved
0.7478	Intermediate Similarity	NPD5739	Approved
0.7478	Intermediate Similarity	NPD6675	Approved
0.7478	Intermediate Similarity	NPD7128	Approved
0.7478	Intermediate Similarity	NPD6402	Approved
0.746	Intermediate Similarity	NPD7078	Approved
0.7458	Intermediate Similarity	NPD6650	Approved
0.7458	Intermediate Similarity	NPD6649	Approved
0.7436	Intermediate Similarity	NPD6373	Approved
0.7436	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6372	Approved
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7414	Intermediate Similarity	NPD5697	Approved
0.7398	Intermediate Similarity	NPD6059	Approved
0.7373	Intermediate Similarity	NPD7290	Approved
0.7373	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7102	Approved
0.7373	Intermediate Similarity	NPD6883	Approved
0.735	Intermediate Similarity	NPD6011	Approved
0.735	Intermediate Similarity	NPD7320	Approved
0.7339	Intermediate Similarity	NPD6079	Approved
0.7339	Intermediate Similarity	NPD6016	Approved
0.7339	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD4632	Approved
0.7315	Intermediate Similarity	NPD5328	Approved
0.7311	Intermediate Similarity	NPD6869	Approved
0.7311	Intermediate Similarity	NPD8130	Phase 1
0.7311	Intermediate Similarity	NPD6847	Approved
0.7311	Intermediate Similarity	NPD6617	Approved
0.7288	Intermediate Similarity	NPD6014	Approved
0.7288	Intermediate Similarity	NPD6012	Approved
0.7288	Intermediate Similarity	NPD6013	Approved
0.728	Intermediate Similarity	NPD5988	Approved
0.7265	Intermediate Similarity	NPD5701	Approved
0.7264	Intermediate Similarity	NPD1694	Approved
0.725	Intermediate Similarity	NPD6053	Discontinued
0.725	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6067	Discontinued
0.7196	Intermediate Similarity	NPD3618	Phase 1
0.7182	Intermediate Similarity	NPD8035	Phase 2
0.7182	Intermediate Similarity	NPD8034	Phase 2
0.7167	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3573	Approved
0.712	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7604	Phase 2
0.708	Intermediate Similarity	NPD4697	Phase 3
0.708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5221	Approved
0.708	Intermediate Similarity	NPD5222	Approved
0.7069	Intermediate Similarity	NPD5211	Phase 2
0.7064	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5983	Phase 2
0.7059	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5286	Approved
0.7043	Intermediate Similarity	NPD4696	Approved
0.7043	Intermediate Similarity	NPD5285	Approved
0.7018	Intermediate Similarity	NPD5173	Approved
0.7018	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD6033	Approved
0.6991	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5223	Approved
0.6977	Remote Similarity	NPD6336	Discontinued
0.6964	Remote Similarity	NPD5778	Approved
0.6964	Remote Similarity	NPD5779	Approved
0.696	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD5141	Approved
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6274	Approved
0.6935	Remote Similarity	NPD6868	Approved
0.6929	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD8074	Phase 3
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6905	Remote Similarity	NPD7100	Approved
0.6905	Remote Similarity	NPD7101	Approved
0.6897	Remote Similarity	NPD4700	Approved
0.6885	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6684	Approved
0.6881	Remote Similarity	NPD7146	Approved
0.6881	Remote Similarity	NPD7334	Approved
0.6881	Remote Similarity	NPD5330	Approved
0.6881	Remote Similarity	NPD6409	Approved
0.6881	Remote Similarity	NPD7521	Approved
0.688	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.687	Remote Similarity	NPD6083	Phase 2
0.687	Remote Similarity	NPD6084	Phase 2
0.6864	Remote Similarity	NPD5175	Approved
0.6864	Remote Similarity	NPD5174	Approved
0.6852	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7260	Phase 2
0.6825	Remote Similarity	NPD6314	Approved
0.6825	Remote Similarity	NPD6313	Approved
0.6822	Remote Similarity	NPD3667	Approved
0.6814	Remote Similarity	NPD4202	Approved
0.681	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD6672	Approved
0.6757	Remote Similarity	NPD5737	Approved
0.6757	Remote Similarity	NPD6903	Approved
0.6723	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD3665	Phase 1
0.6697	Remote Similarity	NPD3133	Approved
0.6697	Remote Similarity	NPD3666	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6695	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD5785	Approved
0.6612	Remote Similarity	NPD4767	Approved
0.6612	Remote Similarity	NPD4768	Approved
0.6579	Remote Similarity	NPD5693	Phase 1
0.6577	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD7645	Phase 2
0.6532	Remote Similarity	NPD5169	Approved
0.6532	Remote Similarity	NPD5248	Approved
0.6532	Remote Similarity	NPD5251	Approved
0.6532	Remote Similarity	NPD5247	Approved
0.6532	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5135	Approved
0.6532	Remote Similarity	NPD5249	Phase 3
0.6532	Remote Similarity	NPD5250	Approved
0.6529	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6914	Discontinued
0.6519	Remote Similarity	NPD7799	Discontinued
0.6504	Remote Similarity	NPD5168	Approved
0.6496	Remote Similarity	NPD7614	Phase 1
0.6481	Remote Similarity	NPD7525	Registered
0.6481	Remote Similarity	NPD4695	Discontinued
0.648	Remote Similarity	NPD5127	Approved
0.648	Remote Similarity	NPD5217	Approved
0.648	Remote Similarity	NPD5215	Approved
0.648	Remote Similarity	NPD5216	Approved
0.6471	Remote Similarity	NPD6648	Approved
0.6466	Remote Similarity	NPD6001	Approved
0.6449	Remote Similarity	NPD6697	Approved
0.6449	Remote Similarity	NPD6114	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