NPASS Compound

Structure

NPC474925 OpenBabel07101719252D 29 32 0 0 1 0 0 0 0 0999 V2000 -2.2301 2.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1058 2.5283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5836 -1.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 2.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5836 1.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 -1.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5836 0.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7918 -0.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3754 0.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1672 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3754 1.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5836 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 0.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 1.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 -1.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9590 -1.3714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1672 -0.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 -1.3714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5836 1.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5836 -0.9143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7918 1.3714 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5836 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7918 0.4571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7918 0.4571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9590 -2.2857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 -2.2857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 19 2 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 2 0 0 0 0 20 22 1 6 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 6 0 0 0 23 25 1 1 0 0 0 24 26 1 6 0 0 0 25 27 1 1 0 0 0 26 27 1 6 0 0 0 27 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.33
Volume:	453.63
LogP:	5.32
LogD:	3.989
LogS:	-5.501
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.35
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	1.305368550674757e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	93.23954010009766%
Volume Distribution (VD):	1.069
Pgp-substrate:	7.291891574859619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.679
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.238
CYP2C9-substrate:	0.226
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	5.99
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.157
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.962
Carcinogencity:	0.88
Eye Corrosion:	0.962
Eye Irritation:	0.87
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC474925

Natural Product ID:	NPC474925
*Common Name:**	12-Deacetylhyrtial
IUPAC Name:	(4aS,4bR,6aS,10aS,10bR,12R,12aR)-12-hydroxy-4a,4b,6a,7,7,10a,10b,12a-octamethyl-4,5,6,8,9,10,11,12-octahydro-1H-chrysene-2-carbaldehyde
Synonyms:	12-Deacetylhyrtial
Standard InCHIKey:	DXWFDFCYGZYCCS-XMBBIXBESA-N
Standard InCHI:	InChI=1S/C27H44O2/c1-21(2)11-9-12-25(6)23(21,4)14-15-26(7)24(5)13-10-19(18-28)16-22(24,3)20(29)17-27(25,26)8/h10,18,20,29H,9,11-17H2,1-8H3/t20-,22+,23+,24-,25+,26+,27-/m1/s1
SMILES:	O=CC1=CC[C@@]2([C@](C1)(C)[C@H](O)C[C@]1([C@@]2(C)CC[C@@]2([C@]1(C)CCCC2(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487993
PubChem CID:	44558953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO5239	Hyrtios erecta	Species	Thorectidae	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
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[507727]

☑ 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 NPC474925 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1350
0.2-0.3	5276
0.3-0.4	12988
0.4-0.5	10760
0.5-0.6	5821
0.6-0.7	4548
0.7-0.8	1509
0.8-0.85	208
0.85-0.9	33
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC206060
0.9213	High Similarity	NPC469545
0.9213	High Similarity	NPC61369
0.9213	High Similarity	NPC5532
0.9059	High Similarity	NPC477579
0.9059	High Similarity	NPC235341
0.9059	High Similarity	NPC95594
0.8989	High Similarity	NPC471207
0.8929	High Similarity	NPC307258
0.8864	High Similarity	NPC85173
0.8864	High Similarity	NPC328141
0.8851	High Similarity	NPC472802
0.8837	High Similarity	NPC158393
0.8824	High Similarity	NPC470812
0.8764	High Similarity	NPC272746
0.875	High Similarity	NPC184663
0.875	High Similarity	NPC472973
0.875	High Similarity	NPC69627
0.8721	High Similarity	NPC133954
0.8681	High Similarity	NPC139570
0.8652	High Similarity	NPC191684
0.8652	High Similarity	NPC183283
0.8636	High Similarity	NPC158778
0.8636	High Similarity	NPC328539
0.8632	High Similarity	NPC95585
0.8632	High Similarity	NPC282233
0.8621	High Similarity	NPC475862
0.8621	High Similarity	NPC74363
0.8621	High Similarity	NPC213412
0.8587	High Similarity	NPC471039
0.8571	High Similarity	NPC23170
0.8571	High Similarity	NPC269729
0.8556	High Similarity	NPC145067
0.8556	High Similarity	NPC472975
0.8556	High Similarity	NPC472978
0.8556	High Similarity	NPC4036
0.8556	High Similarity	NPC233455
0.8556	High Similarity	NPC158030
0.8556	High Similarity	NPC99380
0.8556	High Similarity	NPC65120
0.8539	High Similarity	NPC86319
0.8539	High Similarity	NPC275740
0.8539	High Similarity	NPC472983
0.8523	High Similarity	NPC68160
0.8523	High Similarity	NPC142415
0.8523	High Similarity	NPC18064
0.8523	High Similarity	NPC51700
0.8523	High Similarity	NPC130577
0.8523	High Similarity	NPC98442
0.8523	High Similarity	NPC73064
0.8523	High Similarity	NPC242468
0.8523	High Similarity	NPC171203
0.8523	High Similarity	NPC293564
0.8523	High Similarity	NPC307426
0.8523	High Similarity	NPC88716
0.8523	High Similarity	NPC102683
0.8506	High Similarity	NPC470574
0.8488	Intermediate Similarity	NPC64600
0.8478	Intermediate Similarity	NPC274417
0.8471	Intermediate Similarity	NPC119229
0.8471	Intermediate Similarity	NPC473217
0.8462	Intermediate Similarity	NPC298554
0.8462	Intermediate Similarity	NPC295643
0.8462	Intermediate Similarity	NPC214756
0.8462	Intermediate Similarity	NPC272075
0.8444	Intermediate Similarity	NPC126993
0.8434	Intermediate Similarity	NPC470428
0.8427	Intermediate Similarity	NPC143767
0.8427	Intermediate Similarity	NPC52169
0.8427	Intermediate Similarity	NPC470629
0.8427	Intermediate Similarity	NPC290690
0.8427	Intermediate Similarity	NPC182797
0.8427	Intermediate Similarity	NPC474512
0.8427	Intermediate Similarity	NPC131470
0.8427	Intermediate Similarity	NPC473229
0.8427	Intermediate Similarity	NPC473242
0.8427	Intermediate Similarity	NPC246708
0.8427	Intermediate Similarity	NPC181225
0.8427	Intermediate Similarity	NPC17733
0.8427	Intermediate Similarity	NPC40552
0.8409	Intermediate Similarity	NPC98236
0.8409	Intermediate Similarity	NPC34190
0.8409	Intermediate Similarity	NPC94755
0.8409	Intermediate Similarity	NPC72638
0.8409	Intermediate Similarity	NPC269396
0.8404	Intermediate Similarity	NPC471966
0.8404	Intermediate Similarity	NPC194196
0.8391	Intermediate Similarity	NPC180834
0.8391	Intermediate Similarity	NPC227132
0.8387	Intermediate Similarity	NPC192428
0.8387	Intermediate Similarity	NPC473158
0.8372	Intermediate Similarity	NPC470813
0.8372	Intermediate Similarity	NPC48362
0.837	Intermediate Similarity	NPC472976
0.837	Intermediate Similarity	NPC472977
0.837	Intermediate Similarity	NPC474529
0.837	Intermediate Similarity	NPC209868
0.837	Intermediate Similarity	NPC222047
0.837	Intermediate Similarity	NPC471040
0.8353	Intermediate Similarity	NPC2482
0.8352	Intermediate Similarity	NPC230064
0.8352	Intermediate Similarity	NPC185936
0.8352	Intermediate Similarity	NPC168027
0.8333	Intermediate Similarity	NPC198664
0.8333	Intermediate Similarity	NPC127689
0.8333	Intermediate Similarity	NPC130520
0.8333	Intermediate Similarity	NPC121798
0.8333	Intermediate Similarity	NPC263393
0.8333	Intermediate Similarity	NPC119416
0.8333	Intermediate Similarity	NPC476949
0.8333	Intermediate Similarity	NPC253561
0.8333	Intermediate Similarity	NPC61543
0.8333	Intermediate Similarity	NPC59263
0.8333	Intermediate Similarity	NPC225585
0.8333	Intermediate Similarity	NPC161751
0.8333	Intermediate Similarity	NPC470588
0.8333	Intermediate Similarity	NPC25906
0.8333	Intermediate Similarity	NPC474972
0.8333	Intermediate Similarity	NPC95246
0.8333	Intermediate Similarity	NPC143232
0.8333	Intermediate Similarity	NPC234346
0.8333	Intermediate Similarity	NPC293048
0.8333	Intermediate Similarity	NPC64872
0.8333	Intermediate Similarity	NPC270768
0.8333	Intermediate Similarity	NPC290972
0.8333	Intermediate Similarity	NPC274330
0.8333	Intermediate Similarity	NPC80088
0.8315	Intermediate Similarity	NPC93778
0.8315	Intermediate Similarity	NPC89747
0.8315	Intermediate Similarity	NPC475740
0.8315	Intermediate Similarity	NPC71507
0.8298	Intermediate Similarity	NPC473456
0.828	Intermediate Similarity	NPC148523
0.828	Intermediate Similarity	NPC473170
0.828	Intermediate Similarity	NPC473240
0.8261	Intermediate Similarity	NPC69454
0.8256	Intermediate Similarity	NPC3915
0.8242	Intermediate Similarity	NPC86372
0.8242	Intermediate Similarity	NPC130278
0.8242	Intermediate Similarity	NPC470589
0.8242	Intermediate Similarity	NPC210037
0.8242	Intermediate Similarity	NPC126369
0.8242	Intermediate Similarity	NPC172361
0.8242	Intermediate Similarity	NPC290614
0.8242	Intermediate Similarity	NPC111110
0.8242	Intermediate Similarity	NPC291028
0.8242	Intermediate Similarity	NPC18872
0.8242	Intermediate Similarity	NPC227467
0.8242	Intermediate Similarity	NPC477872
0.8242	Intermediate Similarity	NPC120968
0.8242	Intermediate Similarity	NPC7260
0.8242	Intermediate Similarity	NPC273621
0.8235	Intermediate Similarity	NPC470429
0.8222	Intermediate Similarity	NPC471722
0.8222	Intermediate Similarity	NPC472739
0.8222	Intermediate Similarity	NPC230387
0.8222	Intermediate Similarity	NPC474677
0.8214	Intermediate Similarity	NPC197659
0.8202	Intermediate Similarity	NPC471737
0.8202	Intermediate Similarity	NPC474778
0.8202	Intermediate Similarity	NPC474733
0.8202	Intermediate Similarity	NPC474732
0.8202	Intermediate Similarity	NPC472986
0.8202	Intermediate Similarity	NPC31564
0.8202	Intermediate Similarity	NPC472985
0.8202	Intermediate Similarity	NPC145879
0.8202	Intermediate Similarity	NPC73038
0.8202	Intermediate Similarity	NPC72133
0.8202	Intermediate Similarity	NPC325594
0.8191	Intermediate Similarity	NPC476327
0.8191	Intermediate Similarity	NPC476318
0.8191	Intermediate Similarity	NPC167193
0.8191	Intermediate Similarity	NPC98874
0.8191	Intermediate Similarity	NPC472806
0.8182	Intermediate Similarity	NPC74595
0.8182	Intermediate Similarity	NPC214043
0.8182	Intermediate Similarity	NPC85774
0.8182	Intermediate Similarity	NPC264665
0.8182	Intermediate Similarity	NPC171789
0.8182	Intermediate Similarity	NPC251170
0.8182	Intermediate Similarity	NPC146683
0.8182	Intermediate Similarity	NPC476412
0.8172	Intermediate Similarity	NPC103527
0.8172	Intermediate Similarity	NPC74751
0.8161	Intermediate Similarity	NPC163236
0.8161	Intermediate Similarity	NPC310989
0.8152	Intermediate Similarity	NPC300351
0.8152	Intermediate Similarity	NPC282616
0.8152	Intermediate Similarity	NPC25299
0.8152	Intermediate Similarity	NPC306541
0.8152	Intermediate Similarity	NPC84319
0.8152	Intermediate Similarity	NPC228784
0.8152	Intermediate Similarity	NPC301244
0.8152	Intermediate Similarity	NPC52021
0.8152	Intermediate Similarity	NPC235884
0.8152	Intermediate Similarity	NPC155120
0.8152	Intermediate Similarity	NPC474525
0.8152	Intermediate Similarity	NPC63748
0.8152	Intermediate Similarity	NPC288833
0.8152	Intermediate Similarity	NPC71074

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 NPC474925 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1720
0.2-0.3	3999
0.3-0.4	2261
0.4-0.5	584
0.5-0.6	165
0.6-0.7	137
0.7-0.8	93
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
0.8764	High Similarity	NPD6079	Approved
0.875	High Similarity	NPD5328	Approved
0.8556	High Similarity	NPD7515	Phase 2
0.8409	Intermediate Similarity	NPD3618	Phase 1
0.8387	Intermediate Similarity	NPD4697	Phase 3
0.8191	Intermediate Similarity	NPD5221	Approved
0.8191	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD5222	Approved
0.8172	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD5173	Approved
0.7978	Intermediate Similarity	NPD3666	Approved
0.7978	Intermediate Similarity	NPD4786	Approved
0.7978	Intermediate Similarity	NPD3133	Approved
0.7978	Intermediate Similarity	NPD3665	Phase 1
0.7955	Intermediate Similarity	NPD3667	Approved
0.7938	Intermediate Similarity	NPD4696	Approved
0.7938	Intermediate Similarity	NPD5286	Approved
0.7938	Intermediate Similarity	NPD5285	Approved
0.7917	Intermediate Similarity	NPD4755	Approved
0.7917	Intermediate Similarity	NPD7902	Approved
0.7872	Intermediate Similarity	NPD4202	Approved
0.7857	Intermediate Similarity	NPD5223	Approved
0.7816	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD5224	Approved
0.7778	Intermediate Similarity	NPD5211	Phase 2
0.7778	Intermediate Similarity	NPD5225	Approved
0.7778	Intermediate Similarity	NPD5226	Approved
0.7778	Intermediate Similarity	NPD4633	Approved
0.7755	Intermediate Similarity	NPD4700	Approved
0.7717	Intermediate Similarity	NPD3573	Approved
0.77	Intermediate Similarity	NPD5175	Approved
0.77	Intermediate Similarity	NPD5174	Approved
0.7692	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5141	Approved
0.7604	Intermediate Similarity	NPD7900	Approved
0.7604	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD6881	Approved
0.7573	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD5739	Approved
0.7549	Intermediate Similarity	NPD6675	Approved
0.7549	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD7128	Approved
0.7528	Intermediate Similarity	NPD4695	Discontinued
0.7525	Intermediate Similarity	NPD4754	Approved
0.7476	Intermediate Similarity	NPD5697	Approved
0.7447	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7290	Approved
0.7429	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD6883	Approved
0.7419	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5279	Phase 3
0.7404	Intermediate Similarity	NPD4730	Approved
0.7404	Intermediate Similarity	NPD6011	Approved
0.7404	Intermediate Similarity	NPD5168	Approved
0.7404	Intermediate Similarity	NPD4729	Approved
0.7404	Intermediate Similarity	NPD5128	Approved
0.7404	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD4768	Approved
0.7379	Intermediate Similarity	NPD4767	Approved
0.7368	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD4221	Approved
0.7363	Intermediate Similarity	NPD4223	Phase 3
0.7358	Intermediate Similarity	NPD8130	Phase 1
0.7358	Intermediate Similarity	NPD6617	Approved
0.7358	Intermediate Similarity	NPD6869	Approved
0.7358	Intermediate Similarity	NPD6650	Approved
0.7358	Intermediate Similarity	NPD6649	Approved
0.7358	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6014	Approved
0.7333	Intermediate Similarity	NPD6013	Approved
0.7333	Intermediate Similarity	NPD7525	Registered
0.7333	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7312	Intermediate Similarity	NPD5329	Approved
0.7308	Intermediate Similarity	NPD5701	Approved
0.73	Intermediate Similarity	NPD7638	Approved
0.729	Intermediate Similarity	NPD8297	Approved
0.729	Intermediate Similarity	NPD6882	Approved
0.7283	Intermediate Similarity	NPD4788	Approved
0.7264	Intermediate Similarity	NPD5250	Approved
0.7264	Intermediate Similarity	NPD5248	Approved
0.7264	Intermediate Similarity	NPD5169	Approved
0.7264	Intermediate Similarity	NPD5247	Approved
0.7264	Intermediate Similarity	NPD5249	Phase 3
0.7264	Intermediate Similarity	NPD5251	Approved
0.7264	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5135	Approved
0.7264	Intermediate Similarity	NPD4634	Approved
0.7234	Intermediate Similarity	NPD5330	Approved
0.7234	Intermediate Similarity	NPD7146	Approved
0.7234	Intermediate Similarity	NPD7521	Approved
0.7234	Intermediate Similarity	NPD7334	Approved
0.7234	Intermediate Similarity	NPD6409	Approved
0.7234	Intermediate Similarity	NPD6684	Approved
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7204	Intermediate Similarity	NPD3668	Phase 3
0.7204	Intermediate Similarity	NPD4197	Approved
0.7196	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5216	Approved
0.7196	Intermediate Similarity	NPD5217	Approved
0.7196	Intermediate Similarity	NPD5127	Approved
0.7196	Intermediate Similarity	NPD5215	Approved
0.7188	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4629	Approved
0.7172	Intermediate Similarity	NPD5210	Approved
0.7159	Intermediate Similarity	NPD7339	Approved
0.7159	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7111	Intermediate Similarity	NPD3617	Approved
0.71	Intermediate Similarity	NPD7614	Phase 1
0.7091	Intermediate Similarity	NPD6868	Approved
0.7083	Intermediate Similarity	NPD6903	Approved
0.7079	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4632	Approved
0.7053	Intermediate Similarity	NPD4689	Approved
0.7053	Intermediate Similarity	NPD5690	Phase 2
0.7053	Intermediate Similarity	NPD4690	Approved
0.7053	Intermediate Similarity	NPD5205	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7053	Intermediate Similarity	NPD4688	Approved
0.7053	Intermediate Similarity	NPD4138	Approved
0.7053	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.7041	Intermediate Similarity	NPD6411	Approved
0.703	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD6083	Phase 2
0.7024	Intermediate Similarity	NPD7331	Phase 2
0.7	Intermediate Similarity	NPD5167	Approved
0.6966	Remote Similarity	NPD3703	Phase 2
0.6964	Remote Similarity	NPD6335	Approved
0.6957	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6274	Approved
0.6907	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD6672	Approved
0.6903	Remote Similarity	NPD7100	Approved
0.6903	Remote Similarity	NPD7101	Approved
0.6897	Remote Similarity	NPD4691	Approved
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.6875	Remote Similarity	NPD4694	Approved
0.6875	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD6009	Approved
0.6848	Remote Similarity	NPD4195	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD7507	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6313	Approved
0.6814	Remote Similarity	NPD6314	Approved
0.681	Remote Similarity	NPD8328	Phase 3
0.6796	Remote Similarity	NPD5290	Discontinued
0.6782	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4137	Phase 3
0.6782	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1696	Phase 3
0.6765	Remote Similarity	NPD7732	Phase 3
0.6729	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6723	Remote Similarity	NPD7736	Approved
0.6706	Remote Similarity	NPD7341	Phase 2
0.6705	Remote Similarity	NPD4747	Approved
0.6703	Remote Similarity	NPD6117	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6696	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4058	Approved
0.6638	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6908	Approved
0.6638	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6016	Approved
0.6638	Remote Similarity	NPD6909	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD5696	Approved
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6116	Phase 1
0.661	Remote Similarity	NPD7492	Approved
0.6604	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD1694	Approved
0.6581	Remote Similarity	NPD5988	Approved
0.6559	Remote Similarity	NPD6115	Approved
0.6559	Remote Similarity	NPD6697	Approved
0.6559	Remote Similarity	NPD6114	Approved
0.6559	Remote Similarity	NPD6118	Approved
0.6555	Remote Similarity	NPD6336	Discontinued
0.6555	Remote Similarity	NPD6616	Approved
0.6535	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD5281	Approved
0.6526	Remote Similarity	NPD8028	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