NPASS Compound

Structure

NPC474922 OpenBabel07101719252D 37 40 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 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 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 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 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 5.8564 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 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 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 0.9511 1.3090 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 0.0000 C 0 0 3 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 0.0000 1.0000 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 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 29 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 8 10 1 0 0 0 0 8 20 2 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 14 28 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 18 20 1 0 0 0 0 18 33 1 0 0 0 0 19 37 1 0 0 0 0 21 2 1 1 0 0 0 21 23 1 0 0 0 0 21 26 1 0 0 0 0 22 34 2 0 0 0 0 22 37 1 0 0 0 0 23 30 1 1 0 0 0 24 25 2 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 32 1 1 0 0 0 28 29 1 0 0 0 0 28 36 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 6 0 0 0 32 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.38
Volume:	563.844
LogP:	3.917
LogD:	3.695
LogS:	-4.434
# Rotatable Bonds:	8
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	5.143
Fsp3:	0.844
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:	-5.062
MDCK Permeability:	3.184807792422362e-05
Pgp-inhibitor:	0.791
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	94.01019287109375%
Volume Distribution (VD):	1.224
Pgp-substrate:	1.6157957315444946%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.465
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.616
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	3.022
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.702
Carcinogencity:	0.021
Eye Corrosion:	0.006
Eye Irritation:	0.284
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: NPC474922

Natural Product ID:	NPC474922
*Common Name:**	Colossolactone A
IUPAC Name:	[(3S,5R,10R,13R,14R,17R)-17-[(Z,2S)-3,7-dihydroxy-6-methylhept-5-en-2-yl]-3-hydroxy-4,4,13,14-tetramethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl acetate
Synonyms:
Standard InCHIKey:	UBOFIPWTXMSWDI-ISGKCMTKSA-N
Standard InCHI:	InChI=1S/C32H52O5/c1-20(18-33)8-10-26(35)21(2)23-12-15-31(7)24-9-11-27-29(4,5)28(36)14-17-32(27,19-37-22(3)34)25(24)13-16-30(23,31)6/h8,21,23,26-28,33,35-36H,9-19H2,1-7H3/b20-8-/t21-,23+,26?,27-,28-,30+,31-,32-/m0/s1
SMILES:	CC(C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)COC(=O)C)C)C)C(CC=C(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487868
PubChem CID:	10118664
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.	n.a.	n.a.	PMID[18547117]
NPO31039	Ganoderma colossum	Species	Ganodermataceae	Eukaryota	n.a.	vietnamese	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	=	39.0	ug.mL-1	PMID[502713]

☑ 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 NPC474922 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	160
0.1-0.2	1163
0.2-0.3	4307
0.3-0.4	11393
0.4-0.5	11266
0.5-0.6	6120
0.6-0.7	6019
0.7-0.8	2023
0.8-0.85	183
0.85-0.9	37
0.9-0.95	23
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC276103
0.9556	High Similarity	NPC54248
0.9111	High Similarity	NPC234335
0.9032	High Similarity	NPC141401
0.8977	High Similarity	NPC474970
0.8958	High Similarity	NPC85742
0.8925	High Similarity	NPC304899
0.8925	High Similarity	NPC253115
0.8866	High Similarity	NPC473543
0.8854	High Similarity	NPC476471
0.8854	High Similarity	NPC475344
0.8804	High Similarity	NPC38232
0.8763	High Similarity	NPC474124
0.8763	High Similarity	NPC473523
0.875	High Similarity	NPC475617
0.8737	High Similarity	NPC247233
0.871	High Similarity	NPC119562
0.871	High Similarity	NPC279410
0.8696	High Similarity	NPC477574
0.8696	High Similarity	NPC177641
0.8696	High Similarity	NPC26888
0.8681	High Similarity	NPC246028
0.8646	High Similarity	NPC208358
0.8632	High Similarity	NPC475032
0.8632	High Similarity	NPC475033
0.8632	High Similarity	NPC320306
0.8602	High Similarity	NPC214697
0.8602	High Similarity	NPC27918
0.86	High Similarity	NPC472218
0.86	High Similarity	NPC472217
0.86	High Similarity	NPC472219
0.8587	High Similarity	NPC148414
0.8587	High Similarity	NPC175628
0.8587	High Similarity	NPC111585
0.8587	High Similarity	NPC295668
0.8557	High Similarity	NPC155974
0.8556	High Similarity	NPC477668
0.8556	High Similarity	NPC6391
0.8556	High Similarity	NPC261266
0.8539	High Similarity	NPC102048
0.8526	High Similarity	NPC7124
0.8511	High Similarity	NPC469406
0.8495	Intermediate Similarity	NPC41239
0.8495	Intermediate Similarity	NPC212948
0.8478	Intermediate Similarity	NPC16265
0.8478	Intermediate Similarity	NPC262858
0.8478	Intermediate Similarity	NPC472240
0.8478	Intermediate Similarity	NPC146554
0.8478	Intermediate Similarity	NPC474889
0.8454	Intermediate Similarity	NPC473510
0.8454	Intermediate Similarity	NPC251680
0.8454	Intermediate Similarity	NPC327431
0.8438	Intermediate Similarity	NPC99726
0.8427	Intermediate Similarity	NPC477667
0.8421	Intermediate Similarity	NPC279974
0.8409	Intermediate Similarity	NPC209620
0.8409	Intermediate Similarity	NPC23852
0.8404	Intermediate Similarity	NPC473678
0.8387	Intermediate Similarity	NPC469400
0.8387	Intermediate Similarity	NPC220216
0.8387	Intermediate Similarity	NPC48732
0.8387	Intermediate Similarity	NPC471896
0.8384	Intermediate Similarity	NPC473694
0.8384	Intermediate Similarity	NPC222153
0.8384	Intermediate Similarity	NPC475623
0.8384	Intermediate Similarity	NPC36688
0.8384	Intermediate Similarity	NPC475334
0.837	Intermediate Similarity	NPC470613
0.837	Intermediate Similarity	NPC470612
0.837	Intermediate Similarity	NPC242864
0.8367	Intermediate Similarity	NPC295110
0.8367	Intermediate Similarity	NPC247701
0.8367	Intermediate Similarity	NPC25177
0.8367	Intermediate Similarity	NPC222875
0.8367	Intermediate Similarity	NPC268829
0.8365	Intermediate Similarity	NPC472926
0.8352	Intermediate Similarity	NPC168231
0.8351	Intermediate Similarity	NPC102426
0.8351	Intermediate Similarity	NPC119036
0.8351	Intermediate Similarity	NPC300179
0.8351	Intermediate Similarity	NPC218107
0.8333	Intermediate Similarity	NPC299963
0.8333	Intermediate Similarity	NPC120708
0.8333	Intermediate Similarity	NPC190713
0.8333	Intermediate Similarity	NPC173272
0.8333	Intermediate Similarity	NPC88009
0.8317	Intermediate Similarity	NPC475781
0.8316	Intermediate Similarity	NPC476186
0.8316	Intermediate Similarity	NPC472416
0.8316	Intermediate Similarity	NPC472360
0.8315	Intermediate Similarity	NPC256112
0.8315	Intermediate Similarity	NPC101462
0.8315	Intermediate Similarity	NPC87489
0.8315	Intermediate Similarity	NPC50964
0.8315	Intermediate Similarity	NPC202389
0.8315	Intermediate Similarity	NPC472504
0.83	Intermediate Similarity	NPC181104
0.83	Intermediate Similarity	NPC475331
0.83	Intermediate Similarity	NPC475335
0.83	Intermediate Similarity	NPC80809
0.83	Intermediate Similarity	NPC201144
0.83	Intermediate Similarity	NPC152966
0.83	Intermediate Similarity	NPC121518
0.83	Intermediate Similarity	NPC103298
0.83	Intermediate Similarity	NPC288502
0.8298	Intermediate Similarity	NPC124374
0.8283	Intermediate Similarity	NPC293753
0.8283	Intermediate Similarity	NPC475558
0.8283	Intermediate Similarity	NPC281702
0.8283	Intermediate Similarity	NPC234892
0.8283	Intermediate Similarity	NPC473788
0.828	Intermediate Similarity	NPC314727
0.828	Intermediate Similarity	NPC261320
0.828	Intermediate Similarity	NPC473647
0.8276	Intermediate Similarity	NPC275910
0.8265	Intermediate Similarity	NPC161527
0.8265	Intermediate Similarity	NPC307954
0.8265	Intermediate Similarity	NPC477972
0.8265	Intermediate Similarity	NPC219285
0.8265	Intermediate Similarity	NPC230546
0.8265	Intermediate Similarity	NPC477971
0.8265	Intermediate Similarity	NPC20113
0.8265	Intermediate Similarity	NPC477968
0.8265	Intermediate Similarity	NPC228251
0.8261	Intermediate Similarity	NPC159046
0.8261	Intermediate Similarity	NPC233836
0.8261	Intermediate Similarity	NPC187376
0.8261	Intermediate Similarity	NPC245004
0.8247	Intermediate Similarity	NPC261807
0.8247	Intermediate Similarity	NPC210337
0.8242	Intermediate Similarity	NPC266511
0.8242	Intermediate Similarity	NPC35933
0.8229	Intermediate Similarity	NPC48330
0.8229	Intermediate Similarity	NPC69548
0.8229	Intermediate Similarity	NPC476894
0.8229	Intermediate Similarity	NPC184848
0.8218	Intermediate Similarity	NPC119855
0.8218	Intermediate Similarity	NPC278628
0.8218	Intermediate Similarity	NPC220217
0.8218	Intermediate Similarity	NPC60315
0.8218	Intermediate Similarity	NPC470056
0.8218	Intermediate Similarity	NPC231530
0.8218	Intermediate Similarity	NPC470055
0.8211	Intermediate Similarity	NPC476304
0.8211	Intermediate Similarity	NPC99653
0.8211	Intermediate Similarity	NPC26046
0.8202	Intermediate Similarity	NPC142163
0.82	Intermediate Similarity	NPC97487
0.82	Intermediate Similarity	NPC160583
0.82	Intermediate Similarity	NPC189588
0.82	Intermediate Similarity	NPC10232
0.82	Intermediate Similarity	NPC187302
0.82	Intermediate Similarity	NPC196471
0.8191	Intermediate Similarity	NPC78973
0.8191	Intermediate Similarity	NPC123252
0.8191	Intermediate Similarity	NPC219937
0.8191	Intermediate Similarity	NPC194485
0.8191	Intermediate Similarity	NPC53890
0.8191	Intermediate Similarity	NPC473269
0.8182	Intermediate Similarity	NPC235920
0.8182	Intermediate Similarity	NPC143182
0.8182	Intermediate Similarity	NPC153987
0.8182	Intermediate Similarity	NPC96784
0.8182	Intermediate Similarity	NPC28862
0.8182	Intermediate Similarity	NPC47982
0.8182	Intermediate Similarity	NPC30986
0.8182	Intermediate Similarity	NPC81306
0.8182	Intermediate Similarity	NPC109546
0.8182	Intermediate Similarity	NPC84694
0.8182	Intermediate Similarity	NPC289670
0.8182	Intermediate Similarity	NPC209430
0.8182	Intermediate Similarity	NPC44083
0.8172	Intermediate Similarity	NPC280556
0.8172	Intermediate Similarity	NPC160304
0.8172	Intermediate Similarity	NPC474668
0.8163	Intermediate Similarity	NPC48647
0.8163	Intermediate Similarity	NPC275086
0.8163	Intermediate Similarity	NPC477813
0.8163	Intermediate Similarity	NPC470067
0.8163	Intermediate Similarity	NPC470068
0.8163	Intermediate Similarity	NPC470066
0.8163	Intermediate Similarity	NPC325229
0.8163	Intermediate Similarity	NPC92275
0.8161	Intermediate Similarity	NPC214570
0.8155	Intermediate Similarity	NPC284828
0.8155	Intermediate Similarity	NPC472216
0.8155	Intermediate Similarity	NPC173905
0.8155	Intermediate Similarity	NPC5475
0.8152	Intermediate Similarity	NPC293287
0.8152	Intermediate Similarity	NPC152808
0.8152	Intermediate Similarity	NPC55309
0.8152	Intermediate Similarity	NPC28252
0.8144	Intermediate Similarity	NPC475178
0.8144	Intermediate Similarity	NPC284194
0.8144	Intermediate Similarity	NPC42042
0.8144	Intermediate Similarity	NPC471903
0.8144	Intermediate Similarity	NPC328371
0.8144	Intermediate Similarity	NPC471765
0.8144	Intermediate Similarity	NPC221801
0.8144	Intermediate Similarity	NPC211810

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 NPC474922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1418
0.2-0.3	3972
0.3-0.4	2469
0.4-0.5	659
0.5-0.6	202
0.6-0.7	253
0.7-0.8	36
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD7640	Approved
0.8454	Intermediate Similarity	NPD7639	Approved
0.8351	Intermediate Similarity	NPD7638	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7745	Intermediate Similarity	NPD7632	Discontinued
0.7732	Intermediate Similarity	NPD7637	Suspended
0.7727	Intermediate Similarity	NPD6942	Approved
0.7727	Intermediate Similarity	NPD7339	Approved
0.7692	Intermediate Similarity	NPD7525	Registered
0.7684	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6695	Phase 3
0.7553	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4786	Approved
0.7526	Intermediate Similarity	NPD6051	Approved
0.75	Intermediate Similarity	NPD7750	Discontinued
0.7444	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD6929	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD8033	Approved
0.7358	Intermediate Similarity	NPD6675	Approved
0.7358	Intermediate Similarity	NPD6402	Approved
0.7358	Intermediate Similarity	NPD5739	Approved
0.7358	Intermediate Similarity	NPD7128	Approved
0.7347	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD3667	Approved
0.7333	Intermediate Similarity	NPD8264	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.732	Intermediate Similarity	NPD7524	Approved
0.7312	Intermediate Similarity	NPD6930	Phase 2
0.7312	Intermediate Similarity	NPD6931	Approved
0.73	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD5778	Approved
0.7292	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4225	Approved
0.7281	Intermediate Similarity	NPD8294	Approved
0.7281	Intermediate Similarity	NPD8377	Approved
0.7257	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD7328	Approved
0.7222	Intermediate Similarity	NPD7320	Approved
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD8379	Approved
0.7217	Intermediate Similarity	NPD8296	Approved
0.7217	Intermediate Similarity	NPD8378	Approved
0.7217	Intermediate Similarity	NPD8335	Approved
0.7217	Intermediate Similarity	NPD8380	Approved
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.72	Intermediate Similarity	NPD7515	Phase 2
0.72	Intermediate Similarity	NPD6079	Approved
0.7196	Intermediate Similarity	NPD6008	Approved
0.7193	Intermediate Similarity	NPD7516	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7184	Intermediate Similarity	NPD7902	Approved
0.7182	Intermediate Similarity	NPD8130	Phase 1
0.7174	Intermediate Similarity	NPD5776	Phase 2
0.7174	Intermediate Similarity	NPD6925	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD6373	Approved
0.7156	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7128	Intermediate Similarity	NPD4748	Discontinued
0.7128	Intermediate Similarity	NPD7514	Phase 3
0.7117	Intermediate Similarity	NPD8297	Approved
0.7097	Intermediate Similarity	NPD7145	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7069	Intermediate Similarity	NPD7503	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7053	Intermediate Similarity	NPD6902	Approved
0.7041	Intermediate Similarity	NPD5330	Approved
0.7041	Intermediate Similarity	NPD6409	Approved
0.7041	Intermediate Similarity	NPD6684	Approved
0.7041	Intermediate Similarity	NPD7146	Approved
0.7041	Intermediate Similarity	NPD7521	Approved
0.7041	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD6924	Approved
0.7033	Intermediate Similarity	NPD6926	Approved
0.703	Intermediate Similarity	NPD7087	Discontinued
0.703	Intermediate Similarity	NPD6411	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD5344	Discontinued
0.6964	Remote Similarity	NPD6882	Approved
0.6964	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD4202	Approved
0.6947	Remote Similarity	NPD7332	Phase 2
0.6939	Remote Similarity	NPD6893	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5222	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6907	Remote Similarity	NPD5362	Discontinued
0.69	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6903	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6933	Approved
0.687	Remote Similarity	NPD6009	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6857	Remote Similarity	NPD4755	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD4785	Approved
0.6848	Remote Similarity	NPD4784	Approved
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6837	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3665	Phase 1
0.6833	Remote Similarity	NPD7507	Approved
0.6832	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6412	Phase 2
0.6813	Remote Similarity	NPD7151	Approved
0.6813	Remote Similarity	NPD7152	Approved
0.6813	Remote Similarity	NPD4243	Approved
0.6813	Remote Similarity	NPD7150	Approved
0.6809	Remote Similarity	NPD6932	Approved
0.6807	Remote Similarity	NPD7604	Phase 2
0.68	Remote Similarity	NPD4250	Approved
0.68	Remote Similarity	NPD4251	Approved
0.6792	Remote Similarity	NPD5696	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.6783	Remote Similarity	NPD6868	Approved
0.678	Remote Similarity	NPD5983	Phase 2
0.6778	Remote Similarity	NPD6922	Approved
0.6778	Remote Similarity	NPD6923	Approved
0.6777	Remote Similarity	NPD8293	Discontinued
0.6771	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6686	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6737	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5332	Approved
0.6735	Remote Similarity	NPD5331	Approved
0.6729	Remote Similarity	NPD4700	Approved
0.6729	Remote Similarity	NPD5286	Approved
0.6729	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD6648	Approved
0.6729	Remote Similarity	NPD5285	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.6703	Remote Similarity	NPD7144	Approved
0.6703	Remote Similarity	NPD7143	Approved
0.6702	Remote Similarity	NPD6117	Approved
0.6701	Remote Similarity	NPD4790	Discontinued
0.6701	Remote Similarity	NPD6898	Phase 1
0.67	Remote Similarity	NPD4249	Approved
0.67	Remote Similarity	NPD6098	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD6050	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6683	Phase 2
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6116	Phase 1
0.661	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD7100	Approved
0.6609	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD5225	Approved
0.6606	Remote Similarity	NPD5224	Approved
0.6606	Remote Similarity	NPD5226	Approved
0.6606	Remote Similarity	NPD4633	Approved
0.6602	Remote Similarity	NPD5692	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