NPASS Compound

Structure

NPC475320 OpenBabel07101718242D 40 43 0 0 1 0 0 0 0 0999 V2000 3.8234 -3.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 -5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5144 -2.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2679 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.6840 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2321 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2679 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8671 -3.4272 0.0000 O 0 0 0 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 -0.2321 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2272 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 3 22 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 8 38 1 0 0 0 0 9 11 1 0 0 0 0 9 20 2 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 32 1 0 0 0 0 17 31 1 0 0 0 0 19 33 1 0 0 0 0 19 39 1 0 0 0 0 20 29 1 0 0 0 0 21 2 1 6 0 0 0 21 23 1 0 0 0 0 22 34 2 0 0 0 0 22 39 1 0 0 0 0 23 31 1 6 0 0 0 24 25 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 21 1 1 0 0 0 26 40 1 0 0 0 0 27 30 1 0 0 0 0 27 33 1 6 0 0 0 28 35 2 0 0 0 0 28 38 1 0 0 0 0 29 36 2 0 0 0 0 29 40 1 0 0 0 0 30 37 1 0 0 0 0 31 32 1 6 0 0 0 32 7 1 1 0 0 0 33 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.36
Volume:	593.447
LogP:	4.667
LogD:	3.652
LogS:	-4.755
# Rotatable Bonds:	10
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	5.389
Fsp3:	0.788
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	4.502293450059369e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.834
30% Bioavailability (F30%):	0.9

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	90.6546401977539%
Volume Distribution (VD):	1.875
Pgp-substrate:	1.9806196689605713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.215
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.71
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	3.714
Half-life (T1/2):	0.468

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.441
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.089
Skin Sensitization:	0.082
Carcinogencity:	0.065
Eye Corrosion:	0.009
Eye Irritation:	0.235
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC475320

Natural Product ID:	NPC475320
*Common Name:**	Colossolactone Vii
IUPAC Name:	methyl 3-[(3R,3aR,6R,7R,9bR)-6-(acetyloxymethyl)-7-(2-hydroxypropan-2-yl)-3a,9b-dimethyl-3-[(1S)-1-[(2R)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-1,2,3,4,5,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:	colossolactone VII
Standard InCHIKey:	YIMPDIICGCPBOQ-YPVQYYOHSA-N
Standard InCHI:	InChI=1S/C33H50O7/c1-20-9-11-26(40-29(20)36)21(2)23-13-16-32(7)24-10-12-27(30(4,5)37)33(19-39-22(3)34,18-15-28(35)38-8)25(24)14-17-31(23,32)6/h9,21,23,26-27,37H,10-19H2,1-8H3/t21-,23+,26+,27-,31+,32-,33-/m0/s1
SMILES:	CC1=CCC(OC1=O)C(C)C2CCC3(C2(CCC4=C3CCC(C4(CCC(=O)OC)COC(=O)C)C(C)(C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503417
PubChem CID:	24898464
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	vietnamese	n.a.	PMID[18547117]
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547117]
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19813754]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	=	13.8	ug.mL-1	PMID[480212]

☑ 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 NPC475320 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	196
0.1-0.2	1136
0.2-0.3	4343
0.3-0.4	9673
0.4-0.5	12573
0.5-0.6	6894
0.6-0.7	5936
0.7-0.8	1850
0.8-0.85	71
0.85-0.9	13
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC241221
0.9082	High Similarity	NPC146822
0.8762	High Similarity	NPC236217
0.875	High Similarity	NPC473627
0.8692	High Similarity	NPC190286
0.8687	High Similarity	NPC98868
0.8641	High Similarity	NPC475294
0.8598	High Similarity	NPC474181
0.8586	High Similarity	NPC202705
0.8571	High Similarity	NPC37116
0.8532	High Similarity	NPC153440
0.8519	High Similarity	NPC176840
0.8515	High Similarity	NPC99411
0.8462	Intermediate Similarity	NPC91034
0.8455	Intermediate Similarity	NPC5292
0.8411	Intermediate Similarity	NPC221144
0.8384	Intermediate Similarity	NPC171395
0.8384	Intermediate Similarity	NPC33473
0.8378	Intermediate Similarity	NPC79579
0.8378	Intermediate Similarity	NPC474585
0.8365	Intermediate Similarity	NPC472935
0.8364	Intermediate Similarity	NPC475913
0.835	Intermediate Similarity	NPC180204
0.8333	Intermediate Similarity	NPC310981
0.8317	Intermediate Similarity	NPC197386
0.8304	Intermediate Similarity	NPC46570
0.83	Intermediate Similarity	NPC328371
0.83	Intermediate Similarity	NPC42042
0.8288	Intermediate Similarity	NPC270850
0.8288	Intermediate Similarity	NPC475834
0.8288	Intermediate Similarity	NPC474179
0.8288	Intermediate Similarity	NPC305260
0.8283	Intermediate Similarity	NPC476415
0.8265	Intermediate Similarity	NPC26888
0.8252	Intermediate Similarity	NPC31058
0.8252	Intermediate Similarity	NPC162973
0.8252	Intermediate Similarity	NPC308726
0.8252	Intermediate Similarity	NPC235369
0.8252	Intermediate Similarity	NPC119601
0.8252	Intermediate Similarity	NPC469606
0.8252	Intermediate Similarity	NPC273005
0.8241	Intermediate Similarity	NPC100267
0.8241	Intermediate Similarity	NPC475524
0.8241	Intermediate Similarity	NPC191620
0.8235	Intermediate Similarity	NPC471413
0.8235	Intermediate Similarity	NPC476274
0.823	Intermediate Similarity	NPC107493
0.8224	Intermediate Similarity	NPC197428
0.8224	Intermediate Similarity	NPC29133
0.8208	Intermediate Similarity	NPC220155
0.8208	Intermediate Similarity	NPC189075
0.8208	Intermediate Similarity	NPC275539
0.82	Intermediate Similarity	NPC174948
0.82	Intermediate Similarity	NPC173875
0.82	Intermediate Similarity	NPC469995
0.82	Intermediate Similarity	NPC318282
0.82	Intermediate Similarity	NPC20546
0.82	Intermediate Similarity	NPC281134
0.82	Intermediate Similarity	NPC293052
0.8198	Intermediate Similarity	NPC288679
0.819	Intermediate Similarity	NPC469607
0.8182	Intermediate Similarity	NPC148458
0.8173	Intermediate Similarity	NPC112009
0.8173	Intermediate Similarity	NPC236390
0.8173	Intermediate Similarity	NPC36688
0.8165	Intermediate Similarity	NPC472926
0.8163	Intermediate Similarity	NPC111585
0.8163	Intermediate Similarity	NPC477147
0.8163	Intermediate Similarity	NPC148414
0.8163	Intermediate Similarity	NPC477149
0.8163	Intermediate Similarity	NPC175628
0.8155	Intermediate Similarity	NPC224720
0.8155	Intermediate Similarity	NPC476240
0.8155	Intermediate Similarity	NPC476223
0.8155	Intermediate Similarity	NPC472924
0.8155	Intermediate Similarity	NPC302537
0.8155	Intermediate Similarity	NPC471412
0.8155	Intermediate Similarity	NPC163372
0.8148	Intermediate Similarity	NPC471484
0.8148	Intermediate Similarity	NPC470961
0.8148	Intermediate Similarity	NPC262083
0.8137	Intermediate Similarity	NPC222011
0.8137	Intermediate Similarity	NPC166745
0.8137	Intermediate Similarity	NPC23364
0.8137	Intermediate Similarity	NPC235464
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC304495
0.8131	Intermediate Similarity	NPC5475
0.8125	Intermediate Similarity	NPC475041
0.8119	Intermediate Similarity	NPC29952
0.8119	Intermediate Similarity	NPC472941
0.8119	Intermediate Similarity	NPC456
0.8113	Intermediate Similarity	NPC110496
0.8108	Intermediate Similarity	NPC239273
0.8108	Intermediate Similarity	NPC472934
0.81	Intermediate Similarity	NPC184870
0.8091	Intermediate Similarity	NPC470953
0.8081	Intermediate Similarity	NPC470113
0.8081	Intermediate Similarity	NPC234335
0.8081	Intermediate Similarity	NPC303697
0.8081	Intermediate Similarity	NPC221282
0.8077	Intermediate Similarity	NPC22388
0.8077	Intermediate Similarity	NPC136289
0.8077	Intermediate Similarity	NPC56498
0.8077	Intermediate Similarity	NPC195290
0.8077	Intermediate Similarity	NPC475558
0.8077	Intermediate Similarity	NPC473788
0.8077	Intermediate Similarity	NPC204450
0.8073	Intermediate Similarity	NPC470063
0.8061	Intermediate Similarity	NPC474889
0.8061	Intermediate Similarity	NPC177141
0.8061	Intermediate Similarity	NPC5509
0.8061	Intermediate Similarity	NPC214387
0.8058	Intermediate Similarity	NPC201406
0.8058	Intermediate Similarity	NPC287833
0.8058	Intermediate Similarity	NPC167974
0.8058	Intermediate Similarity	NPC476299
0.8058	Intermediate Similarity	NPC471041
0.8058	Intermediate Similarity	NPC227865
0.8058	Intermediate Similarity	NPC54705
0.8058	Intermediate Similarity	NPC474012
0.8056	Intermediate Similarity	NPC16270
0.8041	Intermediate Similarity	NPC312561
0.8039	Intermediate Similarity	NPC18319
0.8039	Intermediate Similarity	NPC141401
0.8039	Intermediate Similarity	NPC320306
0.8039	Intermediate Similarity	NPC476253
0.8039	Intermediate Similarity	NPC253826
0.8039	Intermediate Similarity	NPC69385
0.8037	Intermediate Similarity	NPC472218
0.8037	Intermediate Similarity	NPC472219
0.8037	Intermediate Similarity	NPC472217
0.802	Intermediate Similarity	NPC317586
0.802	Intermediate Similarity	NPC470016
0.8019	Intermediate Similarity	NPC323834
0.8019	Intermediate Similarity	NPC181265
0.8017	Intermediate Similarity	NPC473635
0.8	Intermediate Similarity	NPC470954
0.8	Intermediate Similarity	NPC38232
0.8	Intermediate Similarity	NPC254202
0.8	Intermediate Similarity	NPC476416
0.8	Intermediate Similarity	NPC474775
0.8	Intermediate Similarity	NPC122056
0.8	Intermediate Similarity	NPC229976
0.8	Intermediate Similarity	NPC475657
0.8	Intermediate Similarity	NPC280566
0.8	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC469789
0.8	Intermediate Similarity	NPC85742
0.8	Intermediate Similarity	NPC472871
0.7982	Intermediate Similarity	NPC214797
0.7982	Intermediate Similarity	NPC231589
0.7982	Intermediate Similarity	NPC324683
0.7982	Intermediate Similarity	NPC284162
0.7982	Intermediate Similarity	NPC255401
0.7982	Intermediate Similarity	NPC118860
0.7982	Intermediate Similarity	NPC67569
0.7982	Intermediate Similarity	NPC474315
0.7981	Intermediate Similarity	NPC475099
0.7981	Intermediate Similarity	NPC474327
0.7981	Intermediate Similarity	NPC244456
0.7981	Intermediate Similarity	NPC298233
0.7981	Intermediate Similarity	NPC469657
0.7981	Intermediate Similarity	NPC81530
0.798	Intermediate Similarity	NPC281942
0.798	Intermediate Similarity	NPC212679
0.798	Intermediate Similarity	NPC232426
0.798	Intermediate Similarity	NPC471896
0.798	Intermediate Similarity	NPC469595
0.798	Intermediate Similarity	NPC476437
0.798	Intermediate Similarity	NPC220454
0.798	Intermediate Similarity	NPC469372
0.798	Intermediate Similarity	NPC476369
0.798	Intermediate Similarity	NPC273199
0.7965	Intermediate Similarity	NPC472933
0.7963	Intermediate Similarity	NPC475274
0.7963	Intermediate Similarity	NPC258543
0.7963	Intermediate Similarity	NPC137911
0.7963	Intermediate Similarity	NPC241927
0.7963	Intermediate Similarity	NPC228477
0.7961	Intermediate Similarity	NPC222303
0.7961	Intermediate Similarity	NPC471717
0.7961	Intermediate Similarity	NPC176845
0.7959	Intermediate Similarity	NPC183546
0.7959	Intermediate Similarity	NPC472870
0.7959	Intermediate Similarity	NPC294480
0.7959	Intermediate Similarity	NPC24816
0.7946	Intermediate Similarity	NPC472927
0.7946	Intermediate Similarity	NPC473656
0.7946	Intermediate Similarity	NPC476959
0.7944	Intermediate Similarity	NPC472925
0.7944	Intermediate Similarity	NPC471601
0.7941	Intermediate Similarity	NPC111684
0.7941	Intermediate Similarity	NPC7124
0.7941	Intermediate Similarity	NPC58052
0.7938	Intermediate Similarity	NPC220478
0.7928	Intermediate Similarity	NPC67259
0.7928	Intermediate Similarity	NPC147912

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 NPC475320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1549
0.2-0.3	3690
0.3-0.4	2452
0.4-0.5	784
0.5-0.6	233
0.6-0.7	239
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8241	Intermediate Similarity	NPD6053	Discontinued
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7961	Intermediate Similarity	NPD7638	Approved
0.7885	Intermediate Similarity	NPD7640	Approved
0.7885	Intermediate Similarity	NPD7639	Approved
0.7843	Intermediate Similarity	NPD5695	Phase 3
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7706	Intermediate Similarity	NPD6881	Approved
0.7706	Intermediate Similarity	NPD6899	Approved
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.7685	Intermediate Similarity	NPD6402	Approved
0.7685	Intermediate Similarity	NPD7128	Approved
0.7685	Intermediate Similarity	NPD5739	Approved
0.7685	Intermediate Similarity	NPD6675	Approved
0.7658	Intermediate Similarity	NPD8130	Phase 1
0.7615	Intermediate Similarity	NPD5697	Approved
0.76	Intermediate Similarity	NPD6672	Approved
0.76	Intermediate Similarity	NPD5737	Approved
0.7589	Intermediate Similarity	NPD8297	Approved
0.7576	Intermediate Similarity	NPD7146	Approved
0.7576	Intermediate Similarity	NPD5330	Approved
0.7576	Intermediate Similarity	NPD7521	Approved
0.7576	Intermediate Similarity	NPD7334	Approved
0.7576	Intermediate Similarity	NPD6409	Approved
0.7576	Intermediate Similarity	NPD6684	Approved
0.7568	Intermediate Similarity	NPD7102	Approved
0.7568	Intermediate Similarity	NPD7290	Approved
0.7568	Intermediate Similarity	NPD6883	Approved
0.7549	Intermediate Similarity	NPD5284	Approved
0.7549	Intermediate Similarity	NPD5693	Phase 1
0.7549	Intermediate Similarity	NPD5281	Approved
0.7545	Intermediate Similarity	NPD6686	Approved
0.7545	Intermediate Similarity	NPD7320	Approved
0.7545	Intermediate Similarity	NPD6011	Approved
0.7526	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7455	Intermediate Similarity	NPD5701	Approved
0.7453	Intermediate Similarity	NPD5696	Approved
0.7434	Intermediate Similarity	NPD6882	Approved
0.7426	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6903	Approved
0.7404	Intermediate Similarity	NPD7748	Approved
0.7379	Intermediate Similarity	NPD6079	Approved
0.7379	Intermediate Similarity	NPD6050	Approved
0.7374	Intermediate Similarity	NPD4786	Approved
0.7368	Intermediate Similarity	NPD4632	Approved
0.7358	Intermediate Similarity	NPD7902	Approved
0.7353	Intermediate Similarity	NPD6904	Approved
0.7353	Intermediate Similarity	NPD6080	Approved
0.7353	Intermediate Similarity	NPD6051	Approved
0.7353	Intermediate Similarity	NPD6673	Approved
0.7353	Intermediate Similarity	NPD5328	Approved
0.7345	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5692	Phase 3
0.7282	Intermediate Similarity	NPD5785	Approved
0.7273	Intermediate Similarity	NPD7507	Approved
0.7258	Intermediate Similarity	NPD7260	Phase 2
0.7248	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD5690	Phase 2
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7222	Intermediate Similarity	NPD5286	Approved
0.7222	Intermediate Similarity	NPD4696	Approved
0.7222	Intermediate Similarity	NPD5285	Approved
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD6411	Approved
0.7212	Intermediate Similarity	NPD5694	Approved
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.72	Intermediate Similarity	NPD3665	Phase 1
0.72	Intermediate Similarity	NPD3133	Approved
0.72	Intermediate Similarity	NPD3666	Approved
0.7196	Intermediate Similarity	NPD4755	Approved
0.7184	Intermediate Similarity	NPD4753	Phase 2
0.7179	Intermediate Similarity	NPD6009	Approved
0.7172	Intermediate Similarity	NPD4221	Approved
0.7172	Intermediate Similarity	NPD4223	Phase 3
0.7172	Intermediate Similarity	NPD3667	Approved
0.717	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.7129	Intermediate Similarity	NPD5329	Approved
0.7129	Intermediate Similarity	NPD1694	Approved
0.7119	Intermediate Similarity	NPD6335	Approved
0.7117	Intermediate Similarity	NPD5141	Approved
0.7115	Intermediate Similarity	NPD6698	Approved
0.7115	Intermediate Similarity	NPD46	Approved
0.7115	Intermediate Similarity	NPD5207	Approved
0.7107	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6371	Approved
0.7103	Intermediate Similarity	NPD5221	Approved
0.7103	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5222	Approved
0.7097	Intermediate Similarity	NPD7319	Approved
0.7094	Intermediate Similarity	NPD6274	Approved
0.7091	Intermediate Similarity	NPD4633	Approved
0.7091	Intermediate Similarity	NPD5225	Approved
0.7091	Intermediate Similarity	NPD5226	Approved
0.7091	Intermediate Similarity	NPD5224	Approved
0.7087	Intermediate Similarity	NPD5208	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.7083	Intermediate Similarity	NPD5983	Phase 2
0.7075	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7900	Approved
0.7064	Intermediate Similarity	NPD4700	Approved
0.7064	Intermediate Similarity	NPD6404	Discontinued
0.7059	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD7100	Approved
0.7059	Intermediate Similarity	NPD5280	Approved
0.7059	Intermediate Similarity	NPD4694	Approved
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD7101	Approved
0.7049	Intermediate Similarity	NPD7492	Approved
0.7048	Intermediate Similarity	NPD7515	Phase 2
0.7037	Intermediate Similarity	NPD5173	Approved
0.7034	Intermediate Similarity	NPD6317	Approved
0.703	Intermediate Similarity	NPD4197	Approved
0.7027	Intermediate Similarity	NPD5174	Approved
0.7027	Intermediate Similarity	NPD5175	Approved
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6101	Approved
0.7016	Intermediate Similarity	NPD7736	Approved
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5210	Approved
0.7009	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6992	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD6314	Approved
0.6975	Remote Similarity	NPD6313	Approved
0.6972	Remote Similarity	NPD4225	Approved
0.6949	Remote Similarity	NPD6868	Approved
0.6944	Remote Similarity	NPD4697	Phase 3
0.6942	Remote Similarity	NPD8033	Approved
0.6939	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8293	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6931	Remote Similarity	NPD5362	Discontinued
0.6929	Remote Similarity	NPD6845	Suspended
0.6893	Remote Similarity	NPD4690	Approved
0.6893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4688	Approved
0.6893	Remote Similarity	NPD4689	Approved
0.6893	Remote Similarity	NPD4693	Phase 3
0.6893	Remote Similarity	NPD4138	Approved
0.6893	Remote Similarity	NPD5205	Approved
0.6887	Remote Similarity	NPD7637	Suspended
0.6885	Remote Similarity	NPD6370	Approved
0.6875	Remote Similarity	NPD4754	Approved
0.6863	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3668	Phase 3
0.686	Remote Similarity	NPD8377	Approved
0.686	Remote Similarity	NPD8294	Approved
0.686	Remote Similarity	NPD6059	Approved
0.6857	Remote Similarity	NPD1695	Approved
0.6857	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5654	Approved
0.6842	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7328	Approved
0.6833	Remote Similarity	NPD7327	Approved
0.6827	Remote Similarity	NPD3573	Approved
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4634	Approved
0.6804	Remote Similarity	NPD8039	Approved
0.6803	Remote Similarity	NPD8379	Approved
0.6803	Remote Similarity	NPD6016	Approved
0.6803	Remote Similarity	NPD8296	Approved
0.6803	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6908	Approved
0.6803	Remote Similarity	NPD8335	Approved
0.6803	Remote Similarity	NPD8380	Approved
0.6803	Remote Similarity	NPD6909	Approved
0.6803	Remote Similarity	NPD8378	Approved
0.6803	Remote Similarity	NPD6015	Approved
0.68	Remote Similarity	NPD4695	Discontinued
0.6796	Remote Similarity	NPD5363	Approved
0.6796	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7838	Discovery
0.6783	Remote Similarity	NPD4730	Approved
0.6783	Remote Similarity	NPD4729	Approved
0.6783	Remote Similarity	NPD5128	Approved
0.678	Remote Similarity	NPD8133	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