NPASS Compound

Structure

CID179208 OpenBabel06191715552D 33 37 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1761 -2.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 32 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 20 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 25 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 27 1 0 0 0 0 15 33 1 0 0 0 0 16 22 1 0 0 0 0 17 28 2 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 24 1 1 0 0 0 19 27 1 0 0 0 0 20 25 1 1 0 0 0 20 27 1 0 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 22 29 2 0 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 23 33 1 0 0 0 0 24 1 1 1 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 26 31 1 0 0 0 0 27 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.25
Volume:	472.325
LogP:	3.834
LogD:	3.141
LogS:	-4.414
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	5.499
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.227
MDCK Permeability:	1.8786120563163422e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.517
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.44
Plasma Protein Binding (PPB):	96.91692352294922%
Volume Distribution (VD):	1.93
Pgp-substrate:	6.22303581237793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.598
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.367
CYP2D6-inhibitor:	0.148
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.61

ADMET: Excretion

Clearance (CL):	15.201
Half-life (T1/2):	0.678

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.624
Carcinogencity:	0.838
Eye Corrosion:	0.005
Eye Irritation:	0.144
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC179208

Natural Product ID:	NPC179208
*Common Name:**	Strongylophorine-26
IUPAC Name:	n.a.
Synonyms:	strongylophorine-26
Standard InCHIKey:	AMOGVPDDGBDGJG-FOMYWIRZSA-N
Standard InCHI:	InChI=1S/C27H36O6/c1-24-10-6-20-25(2)8-5-9-27(20,15-33-23(25)30)19(24)7-11-26(3,31)21(24)13-16-12-17(28)14-18(32-4)22(16)29/h12,14,19-21,31H,5-11,13,15H2,1-4H3/t19-,20-,21-,24+,25-,26-,27-/m0/s1
SMILES:	C[C@@]12CC[C@H]3[C@]4(C)CCC[C@]3(COC4=O)[C@H]1CC[C@@](C)([C@H]2CC1=CC(=O)C=C(C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389231
PubChem CID:	11751458
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350165]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[14695804]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332859]
NPO33317	strongylophora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15332859]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17407351]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25987373]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807132]
NPO33317	strongylophora	n.a.	n.a.	n.a.	n.a.	Philippine	n.a.	PMID[9677282]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[489444]

☑ 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 NPC179208 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	235
0.1-0.2	1454
0.2-0.3	4679
0.3-0.4	9427
0.4-0.5	13198
0.5-0.6	6880
0.6-0.7	4706
0.7-0.8	1798
0.8-0.85	283
0.85-0.9	35
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC473456
0.87	High Similarity	NPC472972
0.8673	High Similarity	NPC147232
0.8646	High Similarity	NPC223093
0.8571	High Similarity	NPC23170
0.8571	High Similarity	NPC74751
0.8544	High Similarity	NPC40170
0.8544	High Similarity	NPC213366
0.85	High Similarity	NPC170131
0.8485	Intermediate Similarity	NPC139570
0.8469	Intermediate Similarity	NPC214756
0.8469	Intermediate Similarity	NPC272075
0.8469	Intermediate Similarity	NPC263780
0.8469	Intermediate Similarity	NPC295643
0.8454	Intermediate Similarity	NPC474209
0.8454	Intermediate Similarity	NPC475823
0.8454	Intermediate Similarity	NPC474728
0.8447	Intermediate Similarity	NPC275583
0.84	Intermediate Similarity	NPC62516
0.84	Intermediate Similarity	NPC157113
0.8396	Intermediate Similarity	NPC27814
0.8384	Intermediate Similarity	NPC477439
0.8367	Intermediate Similarity	NPC474525
0.8367	Intermediate Similarity	NPC470590
0.8367	Intermediate Similarity	NPC233455
0.8367	Intermediate Similarity	NPC4036
0.8367	Intermediate Similarity	NPC60755
0.8367	Intermediate Similarity	NPC470036
0.8367	Intermediate Similarity	NPC77099
0.8367	Intermediate Similarity	NPC285184
0.8367	Intermediate Similarity	NPC248913
0.8367	Intermediate Similarity	NPC174167
0.8367	Intermediate Similarity	NPC158030
0.8367	Intermediate Similarity	NPC65120
0.8367	Intermediate Similarity	NPC145067
0.8333	Intermediate Similarity	NPC104861
0.8333	Intermediate Similarity	NPC30421
0.8317	Intermediate Similarity	NPC26413
0.8316	Intermediate Similarity	NPC6185
0.8316	Intermediate Similarity	NPC474680
0.8316	Intermediate Similarity	NPC241512
0.83	Intermediate Similarity	NPC477437
0.83	Intermediate Similarity	NPC477438
0.83	Intermediate Similarity	NPC274417
0.8283	Intermediate Similarity	NPC477435
0.8283	Intermediate Similarity	NPC477436
0.8269	Intermediate Similarity	NPC95585
0.8269	Intermediate Similarity	NPC282233
0.8265	Intermediate Similarity	NPC120840
0.8265	Intermediate Similarity	NPC113989
0.8265	Intermediate Similarity	NPC328141
0.8265	Intermediate Similarity	NPC46441
0.8241	Intermediate Similarity	NPC43775
0.8235	Intermediate Similarity	NPC478056
0.8235	Intermediate Similarity	NPC471966
0.8235	Intermediate Similarity	NPC260149
0.8235	Intermediate Similarity	NPC58942
0.8218	Intermediate Similarity	NPC327179
0.8218	Intermediate Similarity	NPC98874
0.8208	Intermediate Similarity	NPC44063
0.82	Intermediate Similarity	NPC269729
0.82	Intermediate Similarity	NPC212812
0.82	Intermediate Similarity	NPC474529
0.82	Intermediate Similarity	NPC474963
0.82	Intermediate Similarity	NPC293086
0.82	Intermediate Similarity	NPC160413
0.819	Intermediate Similarity	NPC284865
0.819	Intermediate Similarity	NPC137657
0.8182	Intermediate Similarity	NPC473798
0.8165	Intermediate Similarity	NPC90769
0.8165	Intermediate Similarity	NPC193948
0.8163	Intermediate Similarity	NPC274330
0.8163	Intermediate Similarity	NPC474700
0.8163	Intermediate Similarity	NPC30522
0.8163	Intermediate Similarity	NPC68148
0.8163	Intermediate Similarity	NPC143232
0.8163	Intermediate Similarity	NPC470588
0.8163	Intermediate Similarity	NPC112454
0.8163	Intermediate Similarity	NPC198664
0.8163	Intermediate Similarity	NPC65615
0.8163	Intermediate Similarity	NPC477973
0.8137	Intermediate Similarity	NPC158347
0.8131	Intermediate Similarity	NPC293850
0.8125	Intermediate Similarity	NPC133652
0.8125	Intermediate Similarity	NPC8518
0.8125	Intermediate Similarity	NPC263997
0.8125	Intermediate Similarity	NPC132228
0.8119	Intermediate Similarity	NPC473240
0.8119	Intermediate Similarity	NPC148523
0.8119	Intermediate Similarity	NPC777
0.8119	Intermediate Similarity	NPC195715
0.8113	Intermediate Similarity	NPC478052
0.8108	Intermediate Similarity	NPC152199
0.8108	Intermediate Similarity	NPC96312
0.8108	Intermediate Similarity	NPC40632
0.8108	Intermediate Similarity	NPC134869
0.8108	Intermediate Similarity	NPC328374
0.8108	Intermediate Similarity	NPC235539
0.8108	Intermediate Similarity	NPC251236
0.8105	Intermediate Similarity	NPC105803
0.81	Intermediate Similarity	NPC86368
0.81	Intermediate Similarity	NPC118519
0.81	Intermediate Similarity	NPC79117
0.81	Intermediate Similarity	NPC211230
0.81	Intermediate Similarity	NPC158059
0.81	Intermediate Similarity	NPC202728
0.8095	Intermediate Similarity	NPC90177
0.8095	Intermediate Similarity	NPC478057
0.8095	Intermediate Similarity	NPC95899
0.8081	Intermediate Similarity	NPC111110
0.8081	Intermediate Similarity	NPC126369
0.8081	Intermediate Similarity	NPC291028
0.8081	Intermediate Similarity	NPC470589
0.8077	Intermediate Similarity	NPC118964
0.8073	Intermediate Similarity	NPC146945
0.8073	Intermediate Similarity	NPC171888
0.8073	Intermediate Similarity	NPC34315
0.8061	Intermediate Similarity	NPC470629
0.8061	Intermediate Similarity	NPC181225
0.8061	Intermediate Similarity	NPC290690
0.8061	Intermediate Similarity	NPC474512
0.8061	Intermediate Similarity	NPC182797
0.8061	Intermediate Similarity	NPC40552
0.8061	Intermediate Similarity	NPC246708
0.8061	Intermediate Similarity	NPC230387
0.8061	Intermediate Similarity	NPC17733
0.8061	Intermediate Similarity	NPC52169
0.8061	Intermediate Similarity	NPC473242
0.8058	Intermediate Similarity	NPC475876
0.8056	Intermediate Similarity	NPC2766
0.8056	Intermediate Similarity	NPC41405
0.8041	Intermediate Similarity	NPC73038
0.8039	Intermediate Similarity	NPC305483
0.8039	Intermediate Similarity	NPC471039
0.8039	Intermediate Similarity	NPC476327
0.8039	Intermediate Similarity	NPC476318
0.8039	Intermediate Similarity	NPC96859
0.8039	Intermediate Similarity	NPC328162
0.8037	Intermediate Similarity	NPC202524
0.8037	Intermediate Similarity	NPC475294
0.8021	Intermediate Similarity	NPC96095
0.802	Intermediate Similarity	NPC78580
0.802	Intermediate Similarity	NPC184006
0.802	Intermediate Similarity	NPC6818
0.802	Intermediate Similarity	NPC23621
0.802	Intermediate Similarity	NPC296164
0.802	Intermediate Similarity	NPC471040
0.802	Intermediate Similarity	NPC474328
0.802	Intermediate Similarity	NPC272635
0.802	Intermediate Similarity	NPC148964
0.802	Intermediate Similarity	NPC114159
0.802	Intermediate Similarity	NPC169751
0.802	Intermediate Similarity	NPC191412
0.8018	Intermediate Similarity	NPC18547
0.8018	Intermediate Similarity	NPC474906
0.8	Intermediate Similarity	NPC38754
0.8	Intermediate Similarity	NPC187722
0.8	Intermediate Similarity	NPC136289
0.8	Intermediate Similarity	NPC40918
0.8	Intermediate Similarity	NPC230064
0.8	Intermediate Similarity	NPC105189
0.7982	Intermediate Similarity	NPC239097
0.7981	Intermediate Similarity	NPC475202
0.7981	Intermediate Similarity	NPC475392
0.7981	Intermediate Similarity	NPC475385
0.798	Intermediate Similarity	NPC59263
0.798	Intermediate Similarity	NPC61543
0.798	Intermediate Similarity	NPC293048
0.798	Intermediate Similarity	NPC225585
0.798	Intermediate Similarity	NPC64872
0.798	Intermediate Similarity	NPC290972
0.798	Intermediate Similarity	NPC263393
0.798	Intermediate Similarity	NPC25906
0.798	Intermediate Similarity	NPC270768
0.798	Intermediate Similarity	NPC127689
0.798	Intermediate Similarity	NPC234346
0.798	Intermediate Similarity	NPC121798
0.798	Intermediate Similarity	NPC130520
0.7965	Intermediate Similarity	NPC297179
0.7963	Intermediate Similarity	NPC275539
0.7963	Intermediate Similarity	NPC189075
0.7963	Intermediate Similarity	NPC94529
0.7961	Intermediate Similarity	NPC189880
0.7961	Intermediate Similarity	NPC255589
0.7961	Intermediate Similarity	NPC89225
0.7961	Intermediate Similarity	NPC259788
0.7959	Intermediate Similarity	NPC102683
0.7959	Intermediate Similarity	NPC51700
0.7959	Intermediate Similarity	NPC171203
0.7959	Intermediate Similarity	NPC71507
0.7959	Intermediate Similarity	NPC18064
0.7959	Intermediate Similarity	NPC46912
0.7959	Intermediate Similarity	NPC88716
0.7959	Intermediate Similarity	NPC98442
0.7959	Intermediate Similarity	NPC242468
0.7959	Intermediate Similarity	NPC307426
0.7959	Intermediate Similarity	NPC162107
0.7959	Intermediate Similarity	NPC476932
0.7959	Intermediate Similarity	NPC293564
0.7959	Intermediate Similarity	NPC68160

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 NPC179208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1690
0.2-0.3	3774
0.3-0.4	2237
0.4-0.5	806
0.5-0.6	201
0.6-0.7	143
0.7-0.8	82
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7748	Approved
0.8367	Intermediate Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD3573	Approved
0.8317	Intermediate Similarity	NPD7902	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8286	Intermediate Similarity	NPD6675	Approved
0.8286	Intermediate Similarity	NPD7128	Approved
0.8286	Intermediate Similarity	NPD6402	Approved
0.8286	Intermediate Similarity	NPD5739	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8163	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8131	Intermediate Similarity	NPD7320	Approved
0.8131	Intermediate Similarity	NPD6011	Approved
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6650	Approved
0.8073	Intermediate Similarity	NPD6649	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6372	Approved
0.8056	Intermediate Similarity	NPD6373	Approved
0.8056	Intermediate Similarity	NPD6012	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8037	Intermediate Similarity	NPD5701	Approved
0.802	Intermediate Similarity	NPD7900	Approved
0.802	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7961	Intermediate Similarity	NPD6083	Phase 2
0.7961	Intermediate Similarity	NPD6084	Phase 2
0.7909	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6672	Approved
0.7879	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD4695	Discontinued
0.7767	Intermediate Similarity	NPD5695	Phase 3
0.7714	Intermediate Similarity	NPD5696	Approved
0.7692	Intermediate Similarity	NPD5221	Approved
0.7692	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5222	Approved
0.7652	Intermediate Similarity	NPD6335	Approved
0.7647	Intermediate Similarity	NPD6079	Approved
0.7642	Intermediate Similarity	NPD5286	Approved
0.7642	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5285	Approved
0.7632	Intermediate Similarity	NPD6274	Approved
0.7632	Intermediate Similarity	NPD6868	Approved
0.7627	Intermediate Similarity	NPD8328	Phase 3
0.7624	Intermediate Similarity	NPD6904	Approved
0.7624	Intermediate Similarity	NPD6673	Approved
0.7624	Intermediate Similarity	NPD5328	Approved
0.7624	Intermediate Similarity	NPD6080	Approved
0.7619	Intermediate Similarity	NPD4755	Approved
0.7619	Intermediate Similarity	NPD5173	Approved
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.7573	Intermediate Similarity	NPD6399	Phase 3
0.757	Intermediate Similarity	NPD5223	Approved
0.7565	Intermediate Similarity	NPD6317	Approved
0.7525	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6314	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.7477	Intermediate Similarity	NPD4700	Approved
0.7456	Intermediate Similarity	NPD4632	Approved
0.7431	Intermediate Similarity	NPD5175	Approved
0.7431	Intermediate Similarity	NPD5174	Approved
0.7414	Intermediate Similarity	NPD6009	Approved
0.7377	Intermediate Similarity	NPD7736	Approved
0.7373	Intermediate Similarity	NPD6319	Approved
0.7364	Intermediate Similarity	NPD5141	Approved
0.7358	Intermediate Similarity	NPD7614	Phase 1
0.7333	Intermediate Similarity	NPD7604	Phase 2
0.7327	Intermediate Similarity	NPD3618	Phase 1
0.7327	Intermediate Similarity	NPD6098	Approved
0.7327	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6684	Approved
0.7327	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD7521	Approved
0.7327	Intermediate Similarity	NPD7334	Approved
0.7327	Intermediate Similarity	NPD5330	Approved
0.7311	Intermediate Similarity	NPD6908	Approved
0.7311	Intermediate Similarity	NPD5983	Phase 2
0.7311	Intermediate Similarity	NPD6909	Approved
0.7308	Intermediate Similarity	NPD5693	Phase 1
0.7308	Intermediate Similarity	NPD6050	Approved
0.7308	Intermediate Similarity	NPD6411	Approved
0.7297	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD7492	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7265	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5329	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD7638	Approved
0.7213	Intermediate Similarity	NPD6336	Discontinued
0.7213	Intermediate Similarity	NPD6616	Approved
0.7212	Intermediate Similarity	NPD5692	Phase 3
0.7196	Intermediate Similarity	NPD7732	Phase 3
0.7184	Intermediate Similarity	NPD6903	Approved
0.7168	Intermediate Similarity	NPD4729	Approved
0.7168	Intermediate Similarity	NPD5128	Approved
0.7168	Intermediate Similarity	NPD4730	Approved
0.7167	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7129	Intermediate Similarity	NPD4786	Approved
0.7129	Intermediate Similarity	NPD4197	Approved
0.7115	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6101	Approved
0.7107	Intermediate Similarity	NPD6370	Approved
0.7103	Intermediate Similarity	NPD4629	Approved
0.7103	Intermediate Similarity	NPD5210	Approved
0.71	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.7075	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5247	Approved
0.7043	Intermediate Similarity	NPD5248	Approved
0.7043	Intermediate Similarity	NPD5135	Approved
0.7043	Intermediate Similarity	NPD5169	Approved
0.7043	Intermediate Similarity	NPD5249	Phase 3
0.7043	Intermediate Similarity	NPD5250	Approved
0.7043	Intermediate Similarity	NPD5251	Approved
0.7043	Intermediate Similarity	NPD4634	Approved
0.7043	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3617	Approved
0.7025	Intermediate Similarity	NPD6016	Approved
0.7025	Intermediate Similarity	NPD6015	Approved
0.7018	Intermediate Similarity	NPD5168	Approved
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.699	Remote Similarity	NPD5690	Phase 2
0.6983	Remote Similarity	NPD5217	Approved
0.6983	Remote Similarity	NPD5127	Approved
0.6983	Remote Similarity	NPD5216	Approved
0.6983	Remote Similarity	NPD5215	Approved
0.697	Remote Similarity	NPD7645	Phase 2
0.6967	Remote Similarity	NPD5988	Approved
0.6961	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD3666	Approved
0.6961	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD4223	Phase 3
0.6931	Remote Similarity	NPD4221	Approved
0.6931	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4788	Approved
0.6857	Remote Similarity	NPD5208	Approved
0.6852	Remote Similarity	NPD6001	Approved
0.6827	Remote Similarity	NPD5280	Approved
0.6827	Remote Similarity	NPD5279	Phase 3
0.6827	Remote Similarity	NPD4694	Approved
0.6822	Remote Similarity	NPD5281	Approved
0.6822	Remote Similarity	NPD5284	Approved
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5167	Approved
0.68	Remote Similarity	NPD7507	Approved
0.6796	Remote Similarity	NPD3668	Phase 3
0.6789	Remote Similarity	NPD5654	Approved
0.6783	Remote Similarity	NPD6614	Approved
0.6783	Remote Similarity	NPD6412	Phase 2
0.6757	Remote Similarity	NPD4225	Approved
0.6731	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD5282	Discontinued
0.6693	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD4138	Approved
0.6641	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD4756	Discovery
0.6581	Remote Similarity	NPD6686	Approved
0.6579	Remote Similarity	NPD7632	Discontinued
0.6574	Remote Similarity	NPD5207	Approved
0.6571	Remote Similarity	NPD1696	Phase 3

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