NPASS Compound

Structure

NPC135224 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 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 5.8690 -4.0000 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 5.0029 -3.5000 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 0.5878 0.8090 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 6.7350 -3.5000 0.0000 C 0 0 1 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 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 7.6010 -4.0000 0.0000 O 0 0 0 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 0.0000 -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 7 1 0 0 0 0 6 14 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 29 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 22 1 0 0 0 0 18 26 1 1 0 0 0 19 25 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 1 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:	404.29
Volume:	430.698
LogP:	3.676
LogD:	3.796
LogS:	-4.32
# Rotatable Bonds:	0
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.536
Synthetic Accessibility Score:	5.06
Fsp3:	0.92
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:	-4.769
MDCK Permeability:	2.3023616449791007e-05
Pgp-inhibitor:	0.611
Pgp-substrate:	0.096
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	76.10148620605469%
Volume Distribution (VD):	1.619
Pgp-substrate:	24.309864044189453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.437
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	4.665
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.342
Carcinogencity:	0.056
Eye Corrosion:	0.024
Eye Irritation:	0.284
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC135224

Natural Product ID:	NPC135224
*Common Name:**	(1R,5As,5Br,7Ar,9S,11Ar,11Br,13R,13As,13Bs)-5B,8,8,11A,13A-Pentamethyl-1,3,5,5A,6,7,7A,9,10,11,11B,12,13,13B-Tetradecahydrophenanthro[1,2-G][2]Benzofuran-1,9,13-Triol
IUPAC Name:	(1R,5aS,5bR,7aR,9S,11aR,11bR,13R,13aS,13bS)-5b,8,8,11a,13a-pentamethyl-1,3,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[1,2-g][2]benzofuran-1,9,13-triol
Synonyms:
Standard InCHIKey:	FJUOWUVQEVUWDX-MAVWPOPNSA-N
Standard InCHI:	InChI=1S/C25H40O4/c1-22(2)15-8-10-24(4)16-7-6-14-13-29-21(28)20(14)25(16,5)19(27)12-17(24)23(15,3)11-9-18(22)26/h6,15-21,26-28H,7-13H2,1-5H3/t15-,16-,17+,18-,19+,20+,21+,23-,24-,25+/m0/s1
SMILES:	O[C@@H]1OCC2=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)CC[C@@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495271
PubChem CID:	10668965
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
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.25	ug.mL-1	PMID[470282]

☑ 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 NPC135224 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	197
0.1-0.2	1548
0.2-0.3	4716
0.3-0.4	11562
0.4-0.5	10739
0.5-0.6	6149
0.6-0.7	4985
0.7-0.8	2504
0.8-0.85	258
0.85-0.9	22
0.9-0.95	5
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477969
0.9886	High Similarity	NPC189513
0.9775	High Similarity	NPC100892
0.9775	High Similarity	NPC477970
0.9565	High Similarity	NPC477972
0.9565	High Similarity	NPC219285
0.9565	High Similarity	NPC477971
0.9565	High Similarity	NPC228251
0.9565	High Similarity	NPC20113
0.9565	High Similarity	NPC161527
0.9565	High Similarity	NPC477968
0.9213	High Similarity	NPC470819
0.9167	High Similarity	NPC222161
0.9111	High Similarity	NPC470817
0.9032	High Similarity	NPC94905
0.9032	High Similarity	NPC8954
0.8876	High Similarity	NPC173917
0.8764	High Similarity	NPC119001
0.8673	High Similarity	NPC471888
0.8673	High Similarity	NPC471885
0.8673	High Similarity	NPC473124
0.8673	High Similarity	NPC471886
0.8673	High Similarity	NPC473123
0.8673	High Similarity	NPC471887
0.8587	High Similarity	NPC477917
0.8586	High Similarity	NPC110656
0.8586	High Similarity	NPC203354
0.8586	High Similarity	NPC93352
0.8586	High Similarity	NPC473127
0.8571	High Similarity	NPC300399
0.8571	High Similarity	NPC238397
0.8571	High Similarity	NPC37207
0.8571	High Similarity	NPC471363
0.8571	High Similarity	NPC471889
0.8571	High Similarity	NPC471482
0.8544	High Similarity	NPC194951
0.8544	High Similarity	NPC12046
0.8542	High Similarity	NPC26307
0.8515	High Similarity	NPC80210
0.8515	High Similarity	NPC38376
0.8485	Intermediate Similarity	NPC134270
0.8485	Intermediate Similarity	NPC127933
0.8485	Intermediate Similarity	NPC475889
0.8485	Intermediate Similarity	NPC7644
0.8485	Intermediate Similarity	NPC471450
0.8485	Intermediate Similarity	NPC7613
0.8469	Intermediate Similarity	NPC176406
0.8462	Intermediate Similarity	NPC157441
0.8431	Intermediate Similarity	NPC195116
0.8431	Intermediate Similarity	NPC472901
0.8431	Intermediate Similarity	NPC157530
0.8431	Intermediate Similarity	NPC285253
0.8431	Intermediate Similarity	NPC250089
0.8431	Intermediate Similarity	NPC14630
0.8431	Intermediate Similarity	NPC221110
0.8431	Intermediate Similarity	NPC180459
0.8421	Intermediate Similarity	NPC72817
0.8421	Intermediate Similarity	NPC477927
0.8421	Intermediate Similarity	NPC305160
0.8416	Intermediate Similarity	NPC281939
0.8416	Intermediate Similarity	NPC33053
0.84	Intermediate Similarity	NPC473207
0.84	Intermediate Similarity	NPC470321
0.84	Intermediate Similarity	NPC75608
0.84	Intermediate Similarity	NPC264867
0.84	Intermediate Similarity	NPC201880
0.84	Intermediate Similarity	NPC81567
0.8367	Intermediate Similarity	NPC146188
0.8367	Intermediate Similarity	NPC473790
0.8367	Intermediate Similarity	NPC64348
0.8367	Intermediate Similarity	NPC324841
0.8351	Intermediate Similarity	NPC476893
0.8351	Intermediate Similarity	NPC240372
0.8351	Intermediate Similarity	NPC97867
0.8351	Intermediate Similarity	NPC98112
0.835	Intermediate Similarity	NPC170974
0.835	Intermediate Similarity	NPC103627
0.835	Intermediate Similarity	NPC191439
0.8333	Intermediate Similarity	NPC472189
0.8333	Intermediate Similarity	NPC471372
0.8333	Intermediate Similarity	NPC471362
0.8333	Intermediate Similarity	NPC476894
0.8317	Intermediate Similarity	NPC172867
0.8317	Intermediate Similarity	NPC252296
0.8317	Intermediate Similarity	NPC472899
0.8317	Intermediate Similarity	NPC472900
0.8317	Intermediate Similarity	NPC472898
0.83	Intermediate Similarity	NPC473198
0.83	Intermediate Similarity	NPC162354
0.83	Intermediate Similarity	NPC120009
0.8298	Intermediate Similarity	NPC295668
0.8298	Intermediate Similarity	NPC159876
0.8298	Intermediate Similarity	NPC476226
0.8298	Intermediate Similarity	NPC92885
0.8298	Intermediate Similarity	NPC77796
0.8295	Intermediate Similarity	NPC17550
0.8283	Intermediate Similarity	NPC470434
0.8283	Intermediate Similarity	NPC21568
0.8283	Intermediate Similarity	NPC285231
0.8269	Intermediate Similarity	NPC65034
0.8269	Intermediate Similarity	NPC473021
0.8269	Intermediate Similarity	NPC472987
0.8269	Intermediate Similarity	NPC110494
0.8269	Intermediate Similarity	NPC157474
0.8269	Intermediate Similarity	NPC208189
0.8265	Intermediate Similarity	NPC280825
0.8265	Intermediate Similarity	NPC476895
0.8265	Intermediate Similarity	NPC234287
0.8265	Intermediate Similarity	NPC216260
0.8265	Intermediate Similarity	NPC5358
0.8252	Intermediate Similarity	NPC28844
0.8252	Intermediate Similarity	NPC473318
0.8252	Intermediate Similarity	NPC473328
0.8247	Intermediate Similarity	NPC90583
0.8247	Intermediate Similarity	NPC171598
0.8242	Intermediate Similarity	NPC46320
0.8242	Intermediate Similarity	NPC319238
0.8235	Intermediate Similarity	NPC125423
0.8235	Intermediate Similarity	NPC109376
0.8235	Intermediate Similarity	NPC184512
0.8235	Intermediate Similarity	NPC88013
0.8222	Intermediate Similarity	NPC304285
0.8222	Intermediate Similarity	NPC122945
0.8222	Intermediate Similarity	NPC109938
0.8211	Intermediate Similarity	NPC234335
0.8202	Intermediate Similarity	NPC206062
0.82	Intermediate Similarity	NPC136816
0.8191	Intermediate Similarity	NPC293044
0.8191	Intermediate Similarity	NPC473058
0.819	Intermediate Similarity	NPC231797
0.819	Intermediate Similarity	NPC473125
0.819	Intermediate Similarity	NPC476305
0.8182	Intermediate Similarity	NPC473200
0.8182	Intermediate Similarity	NPC282669
0.8182	Intermediate Similarity	NPC469942
0.8182	Intermediate Similarity	NPC477716
0.8182	Intermediate Similarity	NPC324598
0.8182	Intermediate Similarity	NPC7341
0.8182	Intermediate Similarity	NPC477721
0.8173	Intermediate Similarity	NPC65155
0.8163	Intermediate Similarity	NPC477718
0.8163	Intermediate Similarity	NPC243728
0.8163	Intermediate Similarity	NPC472188
0.8163	Intermediate Similarity	NPC473890
0.8163	Intermediate Similarity	NPC76266
0.8163	Intermediate Similarity	NPC477719
0.8163	Intermediate Similarity	NPC51499
0.8163	Intermediate Similarity	NPC177818
0.8155	Intermediate Similarity	NPC217921
0.8155	Intermediate Similarity	NPC311223
0.8155	Intermediate Similarity	NPC38948
0.8155	Intermediate Similarity	NPC135015
0.8155	Intermediate Similarity	NPC189075
0.8155	Intermediate Similarity	NPC325054
0.8155	Intermediate Similarity	NPC224660
0.8155	Intermediate Similarity	NPC48548
0.8155	Intermediate Similarity	NPC470024
0.8155	Intermediate Similarity	NPC275539
0.8155	Intermediate Similarity	NPC128795
0.8137	Intermediate Similarity	NPC218158
0.8137	Intermediate Similarity	NPC470055
0.8137	Intermediate Similarity	NPC470056
0.8125	Intermediate Similarity	NPC242419
0.8125	Intermediate Similarity	NPC235126
0.8125	Intermediate Similarity	NPC91654
0.8125	Intermediate Similarity	NPC67398
0.8125	Intermediate Similarity	NPC474792
0.8119	Intermediate Similarity	NPC45897
0.8119	Intermediate Similarity	NPC213190
0.8119	Intermediate Similarity	NPC99627
0.8119	Intermediate Similarity	NPC473129
0.8119	Intermediate Similarity	NPC281378
0.8113	Intermediate Similarity	NPC290608
0.8113	Intermediate Similarity	NPC40133
0.8113	Intermediate Similarity	NPC44298
0.8113	Intermediate Similarity	NPC49413
0.8113	Intermediate Similarity	NPC473128
0.8111	Intermediate Similarity	NPC476646
0.8105	Intermediate Similarity	NPC471432
0.8105	Intermediate Similarity	NPC471433
0.81	Intermediate Similarity	NPC129372
0.81	Intermediate Similarity	NPC160734
0.81	Intermediate Similarity	NPC263756
0.81	Intermediate Similarity	NPC474022
0.81	Intermediate Similarity	NPC88000
0.81	Intermediate Similarity	NPC475617
0.81	Intermediate Similarity	NPC476896
0.81	Intermediate Similarity	NPC309425
0.81	Intermediate Similarity	NPC4831
0.81	Intermediate Similarity	NPC47566
0.81	Intermediate Similarity	NPC472023
0.81	Intermediate Similarity	NPC117714
0.81	Intermediate Similarity	NPC477717
0.8095	Intermediate Similarity	NPC13190
0.8081	Intermediate Similarity	NPC471366
0.8081	Intermediate Similarity	NPC472186
0.8081	Intermediate Similarity	NPC477928
0.8081	Intermediate Similarity	NPC158088
0.8081	Intermediate Similarity	NPC476800
0.8081	Intermediate Similarity	NPC473154

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 NPC135224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1667
0.2-0.3	3933
0.3-0.4	2282
0.4-0.5	646
0.5-0.6	242
0.6-0.7	182
0.7-0.8	27
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.79	Intermediate Similarity	NPD7638	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7692	Intermediate Similarity	NPD7645	Phase 2
0.7658	Intermediate Similarity	NPD7327	Approved
0.7658	Intermediate Similarity	NPD7328	Approved
0.7611	Intermediate Similarity	NPD8033	Approved
0.7609	Intermediate Similarity	NPD7525	Registered
0.7589	Intermediate Similarity	NPD7516	Approved
0.7522	Intermediate Similarity	NPD8377	Approved
0.7522	Intermediate Similarity	NPD8294	Approved
0.7456	Intermediate Similarity	NPD8335	Approved
0.7456	Intermediate Similarity	NPD8378	Approved
0.7456	Intermediate Similarity	NPD8380	Approved
0.7456	Intermediate Similarity	NPD8296	Approved
0.7456	Intermediate Similarity	NPD8379	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7304	Intermediate Similarity	NPD7503	Approved
0.7253	Intermediate Similarity	NPD6942	Approved
0.7253	Intermediate Similarity	NPD7339	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7203	Intermediate Similarity	NPD7507	Approved
0.7174	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7632	Discontinued
0.7113	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4225	Approved
0.7025	Intermediate Similarity	NPD7319	Approved
0.701	Intermediate Similarity	NPD6695	Phase 3
0.6991	Remote Similarity	NPD8133	Approved
0.699	Remote Similarity	NPD7748	Approved
0.6961	Remote Similarity	NPD7515	Phase 2
0.6952	Remote Similarity	NPD7902	Approved
0.6939	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD6928	Phase 2
0.681	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6370	Approved
0.6803	Remote Similarity	NPD7736	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6929	Approved
0.6768	Remote Similarity	NPD4786	Approved
0.6765	Remote Similarity	NPD6051	Approved
0.675	Remote Similarity	NPD8328	Phase 3
0.675	Remote Similarity	NPD6067	Discontinued
0.6735	Remote Similarity	NPD3667	Approved
0.6733	Remote Similarity	NPD7524	Approved
0.6733	Remote Similarity	NPD7750	Discontinued
0.6723	Remote Similarity	NPD8516	Approved
0.6723	Remote Similarity	NPD8515	Approved
0.6723	Remote Similarity	NPD8517	Approved
0.6723	Remote Similarity	NPD8513	Phase 3
0.6702	Remote Similarity	NPD8264	Approved
0.6701	Remote Similarity	NPD6931	Approved
0.6701	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6639	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6635	Remote Similarity	NPD8034	Phase 2
0.6635	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD3618	Phase 1
0.6606	Remote Similarity	NPD5344	Discontinued
0.6602	Remote Similarity	NPD5328	Approved
0.6596	Remote Similarity	NPD6926	Approved
0.6596	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD8293	Discontinued
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8171	Discontinued
0.6562	Remote Similarity	NPD5776	Phase 2
0.6562	Remote Similarity	NPD6925	Approved
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7332	Phase 2
0.6531	Remote Similarity	NPD7514	Phase 3
0.6531	Remote Similarity	NPD7509	Discontinued
0.6518	Remote Similarity	NPD6675	Approved
0.6518	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD6402	Approved
0.6518	Remote Similarity	NPD7128	Approved
0.6518	Remote Similarity	NPD5739	Approved
0.6495	Remote Similarity	NPD7145	Approved
0.6476	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD7087	Discontinued
0.6476	Remote Similarity	NPD7637	Suspended
0.6466	Remote Similarity	NPD6882	Approved
0.6465	Remote Similarity	NPD6902	Approved
0.6458	Remote Similarity	NPD6933	Approved
0.6455	Remote Similarity	NPD4159	Approved
0.6446	Remote Similarity	NPD6016	Approved
0.6446	Remote Similarity	NPD6015	Approved
0.6423	Remote Similarity	NPD7492	Approved
0.6421	Remote Similarity	NPD4784	Approved
0.6421	Remote Similarity	NPD4785	Approved
0.6415	Remote Similarity	NPD4202	Approved
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6404	Remote Similarity	NPD7320	Approved
0.6393	Remote Similarity	NPD5988	Approved
0.6392	Remote Similarity	NPD6932	Approved
0.6387	Remote Similarity	NPD6009	Approved
0.6383	Remote Similarity	NPD7152	Approved
0.6383	Remote Similarity	NPD7151	Approved
0.6383	Remote Similarity	NPD4243	Approved
0.6383	Remote Similarity	NPD7150	Approved
0.6381	Remote Similarity	NPD3168	Discontinued
0.6373	Remote Similarity	NPD6893	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD4748	Discontinued
0.6364	Remote Similarity	NPD6648	Approved
0.6348	Remote Similarity	NPD6372	Approved
0.6348	Remote Similarity	NPD6373	Approved
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6922	Approved
0.6344	Remote Similarity	NPD6923	Approved
0.633	Remote Similarity	NPD4755	Approved
0.6328	Remote Similarity	NPD8449	Approved
0.6327	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6053	Discontinued
0.632	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD5701	Approved
0.63	Remote Similarity	NPD6898	Phase 1
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.6279	Remote Similarity	NPD8450	Suspended
0.6277	Remote Similarity	NPD7143	Approved
0.6277	Remote Similarity	NPD7144	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD3668	Phase 3
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD3665	Phase 1
0.6271	Remote Similarity	NPD4632	Approved
0.627	Remote Similarity	NPD6033	Approved
0.6263	Remote Similarity	NPD6683	Phase 2
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.6261	Remote Similarity	NPD6011	Approved
0.6261	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD5222	Approved
0.6239	Remote Similarity	NPD5221	Approved
0.6239	Remote Similarity	NPD4697	Phase 3
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6869	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6238	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.6214	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.6204	Remote Similarity	NPD7625	Phase 1
0.6186	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD5173	Approved
0.6182	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6411	Approved
0.6161	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.614	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD5125	Phase 3
0.6129	Remote Similarity	NPD5126	Approved
0.6126	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD368	Approved
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4633	Approved
0.6106	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD7741	Discontinued
0.6087	Remote Similarity	NPD6640	Phase 3
0.6082	Remote Similarity	NPD1810	Approved
0.6082	Remote Similarity	NPD1811	Approved
0.608	Remote Similarity	NPD7604	Phase 2
0.6075	Remote Similarity	NPD7838	Discovery
0.6075	Remote Similarity	NPD6698	Approved
0.6075	Remote Similarity	NPD46	Approved
0.6063	Remote Similarity	NPD8074	Phase 3
0.6053	Remote Similarity	NPD4754	Approved
0.6053	Remote Similarity	NPD5175	Approved
0.6053	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD5983	Phase 2

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