NPASS Compound

Structure

NPC165250 OpenBabel07101718242D 32 36 0 0 1 0 0 0 0 0999 V2000 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 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 0.5878 0.8090 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 2.4049 1.0000 0.0000 C 0 0 1 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 4.1369 -2.0000 0.0000 C 0 0 2 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 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 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 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 1 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 3.2709 3.5000 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 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 31 1 0 0 0 0 15 28 2 0 0 0 0 15 32 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 32 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	468.808
LogP:	4.807
LogD:	4.102
LogS:	-4.633
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.945
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.878
MDCK Permeability:	2.4978169676614925e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.07
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.362
Plasma Protein Binding (PPB):	94.68463897705078%
Volume Distribution (VD):	1.351
Pgp-substrate:	6.6950812339782715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.615
CYP2C9-inhibitor:	0.29
CYP2C9-substrate:	0.497
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.389
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	7.977
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.35
Carcinogencity:	0.309
Eye Corrosion:	0.022
Eye Irritation:	0.265
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC165250

Natural Product ID:	NPC165250
*Common Name:**	Sesterstatin 7
IUPAC Name:	[(4S,5aS,5bR,7aS,11aS,11bR,13R,13aS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1-oxo-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[2,1-e][2]benzofuran-4-yl] acetate
Synonyms:	16-Beta-Acetoxyscalarolide
Standard InCHIKey:	LOCDSBKFSVHNIV-XPSVZDKBSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-15(28)32-17-12-20-26(5)11-8-18-24(2,3)9-7-10-25(18,4)19(26)13-21(29)27(20,6)22-16(17)14-31-23(22)30/h17-21,29H,7-14H2,1-6H3/t17-,18-,19+,20-,21+,25-,26+,27+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@](C3=C1COC3=O)(C)[C@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456095
PubChem CID:	5324503
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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	63.0	%	PMID[449405]

☑ 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 NPC165250 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	243
0.1-0.2	1472
0.2-0.3	4278
0.3-0.4	7646
0.4-0.5	13189
0.5-0.6	6389
0.6-0.7	5704
0.7-0.8	3498
0.8-0.85	226
0.85-0.9	33
0.9-0.95	10
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC175351
0.9574	High Similarity	NPC132753
0.9574	High Similarity	NPC121402
0.9574	High Similarity	NPC151681
0.9574	High Similarity	NPC224356
0.9495	High Similarity	NPC325054
0.9485	High Similarity	NPC471208
0.9468	High Similarity	NPC154526
0.9468	High Similarity	NPC472363
0.9468	High Similarity	NPC472362
0.9208	High Similarity	NPC31522
0.9109	High Similarity	NPC275539
0.9109	High Similarity	NPC189075
0.9109	High Similarity	NPC90946
0.9109	High Similarity	NPC300614
0.901	High Similarity	NPC110496
0.899	High Similarity	NPC476081
0.89	High Similarity	NPC159533
0.88	High Similarity	NPC295791
0.8762	High Similarity	NPC194951
0.8762	High Similarity	NPC12046
0.8713	High Similarity	NPC478057
0.8713	High Similarity	NPC120321
0.8713	High Similarity	NPC254202
0.8679	High Similarity	NPC25909
0.8679	High Similarity	NPC157441
0.8641	High Similarity	NPC67321
0.8641	High Similarity	NPC187435
0.8614	High Similarity	NPC469606
0.8614	High Similarity	NPC31058
0.8614	High Similarity	NPC273005
0.86	High Similarity	NPC47024
0.8586	High Similarity	NPC51499
0.8585	High Similarity	NPC277769
0.8544	High Similarity	NPC34768
0.8544	High Similarity	NPC469607
0.8529	High Similarity	NPC95899
0.8515	High Similarity	NPC471412
0.8515	High Similarity	NPC471075
0.85	High Similarity	NPC325229
0.85	High Similarity	NPC216478
0.85	High Similarity	NPC275086
0.8485	Intermediate Similarity	NPC134072
0.8485	Intermediate Similarity	NPC234993
0.8476	Intermediate Similarity	NPC299590
0.8462	Intermediate Similarity	NPC143609
0.8447	Intermediate Similarity	NPC222161
0.8431	Intermediate Similarity	NPC137430
0.8431	Intermediate Similarity	NPC162973
0.8416	Intermediate Similarity	NPC471413
0.8416	Intermediate Similarity	NPC476299
0.8416	Intermediate Similarity	NPC251680
0.8416	Intermediate Similarity	NPC476767
0.8416	Intermediate Similarity	NPC474012
0.8411	Intermediate Similarity	NPC269530
0.8411	Intermediate Similarity	NPC470063
0.8411	Intermediate Similarity	NPC90952
0.8411	Intermediate Similarity	NPC4573
0.8396	Intermediate Similarity	NPC472666
0.8384	Intermediate Similarity	NPC157686
0.8384	Intermediate Similarity	NPC276110
0.8384	Intermediate Similarity	NPC259042
0.8381	Intermediate Similarity	NPC306265
0.8381	Intermediate Similarity	NPC469916
0.8381	Intermediate Similarity	NPC472439
0.8367	Intermediate Similarity	NPC472640
0.8367	Intermediate Similarity	NPC472641
0.8367	Intermediate Similarity	NPC139692
0.8365	Intermediate Similarity	NPC111952
0.8365	Intermediate Similarity	NPC478208
0.835	Intermediate Similarity	NPC474822
0.835	Intermediate Similarity	NPC36688
0.835	Intermediate Similarity	NPC99266
0.835	Intermediate Similarity	NPC8196
0.835	Intermediate Similarity	NPC112009
0.8333	Intermediate Similarity	NPC235142
0.8318	Intermediate Similarity	NPC469655
0.8318	Intermediate Similarity	NPC474846
0.8318	Intermediate Similarity	NPC469656
0.8317	Intermediate Similarity	NPC478056
0.8316	Intermediate Similarity	NPC250981
0.8302	Intermediate Similarity	NPC476759
0.8302	Intermediate Similarity	NPC112457
0.83	Intermediate Similarity	NPC7124
0.8286	Intermediate Similarity	NPC473586
0.8286	Intermediate Similarity	NPC179380
0.8286	Intermediate Similarity	NPC469318
0.8286	Intermediate Similarity	NPC302788
0.8286	Intermediate Similarity	NPC475570
0.8286	Intermediate Similarity	NPC473173
0.8283	Intermediate Similarity	NPC469596
0.8283	Intermediate Similarity	NPC148000
0.8283	Intermediate Similarity	NPC105490
0.8283	Intermediate Similarity	NPC91010
0.8283	Intermediate Similarity	NPC225474
0.8273	Intermediate Similarity	NPC134430
0.8273	Intermediate Similarity	NPC473968
0.8273	Intermediate Similarity	NPC55296
0.8265	Intermediate Similarity	NPC477574
0.8265	Intermediate Similarity	NPC235704
0.8265	Intermediate Similarity	NPC41239
0.8257	Intermediate Similarity	NPC110861
0.8252	Intermediate Similarity	NPC476890
0.8252	Intermediate Similarity	NPC58329
0.8252	Intermediate Similarity	NPC476769
0.8241	Intermediate Similarity	NPC476163
0.8241	Intermediate Similarity	NPC42658
0.8235	Intermediate Similarity	NPC477971
0.8235	Intermediate Similarity	NPC228251
0.8235	Intermediate Similarity	NPC20113
0.8235	Intermediate Similarity	NPC477968
0.8235	Intermediate Similarity	NPC201406
0.8235	Intermediate Similarity	NPC117685
0.8235	Intermediate Similarity	NPC477972
0.8235	Intermediate Similarity	NPC161527
0.8235	Intermediate Similarity	NPC307954
0.8235	Intermediate Similarity	NPC219285
0.8229	Intermediate Similarity	NPC471779
0.8224	Intermediate Similarity	NPC478209
0.8218	Intermediate Similarity	NPC91695
0.8218	Intermediate Similarity	NPC476879
0.8218	Intermediate Similarity	NPC473963
0.8218	Intermediate Similarity	NPC70145
0.8218	Intermediate Similarity	NPC476878
0.8214	Intermediate Similarity	NPC251226
0.8214	Intermediate Similarity	NPC268530
0.8214	Intermediate Similarity	NPC154491
0.8208	Intermediate Similarity	NPC475263
0.8208	Intermediate Similarity	NPC473483
0.8208	Intermediate Similarity	NPC476479
0.8208	Intermediate Similarity	NPC476765
0.82	Intermediate Similarity	NPC183012
0.82	Intermediate Similarity	NPC474727
0.819	Intermediate Similarity	NPC88349
0.819	Intermediate Similarity	NPC220217
0.819	Intermediate Similarity	NPC119855
0.819	Intermediate Similarity	NPC478052
0.8182	Intermediate Similarity	NPC229281
0.8182	Intermediate Similarity	NPC7349
0.8182	Intermediate Similarity	NPC110022
0.8182	Intermediate Similarity	NPC99653
0.8182	Intermediate Similarity	NPC268954
0.8182	Intermediate Similarity	NPC44170
0.8182	Intermediate Similarity	NPC199543
0.8173	Intermediate Similarity	NPC324001
0.8173	Intermediate Similarity	NPC180204
0.8173	Intermediate Similarity	NPC476889
0.8173	Intermediate Similarity	NPC95585
0.8173	Intermediate Similarity	NPC282233
0.8173	Intermediate Similarity	NPC45897
0.8163	Intermediate Similarity	NPC472642
0.8163	Intermediate Similarity	NPC78973
0.8155	Intermediate Similarity	NPC93744
0.8155	Intermediate Similarity	NPC11974
0.8155	Intermediate Similarity	NPC97435
0.8155	Intermediate Similarity	NPC303559
0.8155	Intermediate Similarity	NPC476888
0.8155	Intermediate Similarity	NPC63249
0.8142	Intermediate Similarity	NPC4021
0.8142	Intermediate Similarity	NPC67569
0.8142	Intermediate Similarity	NPC159456
0.8137	Intermediate Similarity	NPC475876
0.8137	Intermediate Similarity	NPC164349
0.8137	Intermediate Similarity	NPC222303
0.8137	Intermediate Similarity	NPC234617
0.8137	Intermediate Similarity	NPC260149
0.8137	Intermediate Similarity	NPC124703
0.8137	Intermediate Similarity	NPC58942
0.8131	Intermediate Similarity	NPC5475
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC478210
0.8125	Intermediate Similarity	NPC476529
0.8125	Intermediate Similarity	NPC473636
0.8125	Intermediate Similarity	NPC230513
0.8125	Intermediate Similarity	NPC475041
0.8125	Intermediate Similarity	NPC475775
0.8125	Intermediate Similarity	NPC42673
0.8125	Intermediate Similarity	NPC77689
0.8119	Intermediate Similarity	NPC29952
0.8119	Intermediate Similarity	NPC116457
0.8119	Intermediate Similarity	NPC165632
0.8119	Intermediate Similarity	NPC476327
0.8119	Intermediate Similarity	NPC476318
0.8119	Intermediate Similarity	NPC473964
0.8119	Intermediate Similarity	NPC327179
0.8119	Intermediate Similarity	NPC93245
0.8119	Intermediate Similarity	NPC242848
0.8119	Intermediate Similarity	NPC202833
0.8113	Intermediate Similarity	NPC301666
0.8108	Intermediate Similarity	NPC475809
0.8108	Intermediate Similarity	NPC473590
0.8108	Intermediate Similarity	NPC474483
0.8105	Intermediate Similarity	NPC32223
0.81	Intermediate Similarity	NPC191412
0.81	Intermediate Similarity	NPC57117
0.81	Intermediate Similarity	NPC474554
0.81	Intermediate Similarity	NPC159365
0.81	Intermediate Similarity	NPC471720

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 NPC165250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1762
0.2-0.3	3592
0.3-0.4	2275
0.4-0.5	804
0.5-0.6	258
0.6-0.7	186
0.7-0.8	53
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
0.85	High Similarity	NPD7638	Approved
0.8476	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8416	Intermediate Similarity	NPD7639	Approved
0.8416	Intermediate Similarity	NPD7640	Approved
0.8396	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD7632	Discontinued
0.8113	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD7902	Approved
0.7921	Intermediate Similarity	NPD7748	Approved
0.79	Intermediate Similarity	NPD7515	Phase 2
0.787	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7745	Intermediate Similarity	NPD7900	Approved
0.7745	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7507	Approved
0.7647	Intermediate Similarity	NPD6399	Phase 3
0.7636	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4225	Approved
0.7549	Intermediate Similarity	NPD8035	Phase 2
0.7549	Intermediate Similarity	NPD8034	Phase 2
0.7523	Intermediate Similarity	NPD7128	Approved
0.7523	Intermediate Similarity	NPD6402	Approved
0.7523	Intermediate Similarity	NPD5739	Approved
0.7523	Intermediate Similarity	NPD6675	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.7478	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7414	Intermediate Similarity	NPD7328	Approved
0.7414	Intermediate Similarity	NPD7327	Approved
0.74	Intermediate Similarity	NPD3618	Phase 1
0.7387	Intermediate Similarity	NPD6881	Approved
0.7387	Intermediate Similarity	NPD6899	Approved
0.7387	Intermediate Similarity	NPD7320	Approved
0.7373	Intermediate Similarity	NPD8033	Approved
0.7364	Intermediate Similarity	NPD6008	Approved
0.735	Intermediate Similarity	NPD7516	Approved
0.7347	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6650	Approved
0.7345	Intermediate Similarity	NPD6649	Approved
0.73	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD1694	Approved
0.7297	Intermediate Similarity	NPD5697	Approved
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.7297	Intermediate Similarity	NPD5701	Approved
0.7288	Intermediate Similarity	NPD8294	Approved
0.7288	Intermediate Similarity	NPD8377	Approved
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7257	Intermediate Similarity	NPD6883	Approved
0.7257	Intermediate Similarity	NPD7102	Approved
0.7257	Intermediate Similarity	NPD7290	Approved
0.7255	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7232	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8379	Approved
0.7227	Intermediate Similarity	NPD8378	Approved
0.7227	Intermediate Similarity	NPD8335	Approved
0.7227	Intermediate Similarity	NPD8296	Approved
0.7227	Intermediate Similarity	NPD8380	Approved
0.7217	Intermediate Similarity	NPD8133	Approved
0.7196	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD6083	Phase 2
0.7193	Intermediate Similarity	NPD6869	Approved
0.7193	Intermediate Similarity	NPD6617	Approved
0.7193	Intermediate Similarity	NPD8130	Phase 1
0.7193	Intermediate Similarity	NPD6847	Approved
0.7184	Intermediate Similarity	NPD5328	Approved
0.7168	Intermediate Similarity	NPD6012	Approved
0.7168	Intermediate Similarity	NPD6013	Approved
0.7168	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.7115	Intermediate Similarity	NPD6698	Approved
0.7115	Intermediate Similarity	NPD46	Approved
0.7113	Intermediate Similarity	NPD6118	Approved
0.7113	Intermediate Similarity	NPD6115	Approved
0.7113	Intermediate Similarity	NPD6114	Approved
0.7113	Intermediate Similarity	NPD6697	Approved
0.708	Intermediate Similarity	NPD6011	Approved
0.7069	Intermediate Similarity	NPD4632	Approved
0.7059	Intermediate Similarity	NPD7521	Approved
0.7059	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD6684	Approved
0.7059	Intermediate Similarity	NPD5330	Approved
0.7059	Intermediate Similarity	NPD6409	Approved
0.7059	Intermediate Similarity	NPD7146	Approved
0.7048	Intermediate Similarity	NPD6079	Approved
0.7043	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4755	Approved
0.703	Intermediate Similarity	NPD4786	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7736	Approved
0.701	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD6319	Approved
0.6981	Remote Similarity	NPD5778	Approved
0.6981	Remote Similarity	NPD4202	Approved
0.6981	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD5696	Approved
0.6944	Remote Similarity	NPD4697	Phase 3
0.6942	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD5211	Phase 2
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6911	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD4696	Approved
0.6909	Remote Similarity	NPD5285	Approved
0.6909	Remote Similarity	NPD5286	Approved
0.6909	Remote Similarity	NPD4700	Approved
0.6907	Remote Similarity	NPD6117	Approved
0.6891	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD7645	Phase 2
0.6863	Remote Similarity	NPD3665	Phase 1
0.6863	Remote Similarity	NPD3133	Approved
0.6863	Remote Similarity	NPD3666	Approved
0.686	Remote Similarity	NPD6054	Approved
0.686	Remote Similarity	NPD6059	Approved
0.6855	Remote Similarity	NPD6616	Approved
0.6852	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD3573	Approved
0.6814	Remote Similarity	NPD5141	Approved
0.681	Remote Similarity	NPD6371	Approved
0.6807	Remote Similarity	NPD6274	Approved
0.6803	Remote Similarity	NPD5983	Phase 2
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD8293	Discontinued
0.68	Remote Similarity	NPD7078	Approved
0.6789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5222	Approved
0.6789	Remote Similarity	NPD5221	Approved
0.6786	Remote Similarity	NPD5224	Approved
0.6786	Remote Similarity	NPD5226	Approved
0.6786	Remote Similarity	NPD4633	Approved
0.6786	Remote Similarity	NPD5225	Approved
0.6777	Remote Similarity	NPD7101	Approved
0.6777	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD6370	Approved
0.6731	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5693	Phase 1
0.6729	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD5173	Approved
0.6726	Remote Similarity	NPD5174	Approved
0.6726	Remote Similarity	NPD5175	Approved
0.672	Remote Similarity	NPD6336	Discontinued
0.6701	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5223	Approved
0.6694	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.6634	Remote Similarity	NPD7525	Registered
0.6613	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD4767	Approved
0.6607	Remote Similarity	NPD6648	Approved
0.66	Remote Similarity	NPD3617	Approved
0.6589	Remote Similarity	NPD7260	Phase 2
0.6579	Remote Similarity	NPD4754	Approved
0.6574	Remote Similarity	NPD5281	Approved
0.6574	Remote Similarity	NPD5284	Approved
0.656	Remote Similarity	NPD6067	Discontinued
0.6557	Remote Similarity	NPD6313	Approved
0.6557	Remote Similarity	NPD6314	Approved
0.6552	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4629	Approved
0.6545	Remote Similarity	NPD5210	Approved
0.6542	Remote Similarity	NPD6673	Approved
0.6542	Remote Similarity	NPD6051	Approved
0.6542	Remote Similarity	NPD6080	Approved
0.6542	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD3668	Phase 3
0.6538	Remote Similarity	NPD6845	Suspended
0.6532	Remote Similarity	NPD6921	Approved
0.6532	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4730	Approved
0.6496	Remote Similarity	NPD4729	Approved
0.6496	Remote Similarity	NPD5128	Approved
0.6486	Remote Similarity	NPD7614	Phase 1
0.6481	Remote Similarity	NPD7838	Discovery
0.6471	Remote Similarity	NPD4695	Discontinued
0.6465	Remote Similarity	NPD3703	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