NPASS Compound

Structure

NPC476033 OpenBabel07101718192D 28 31 0 0 1 0 0 0 0 0999 V2000 6.1667 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -4.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 0.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9706 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4268 1.0443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 -2.3794 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 1.8366 -0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 -0.4502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 15 20 1 0 0 0 0 16 13 1 1 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 25 1 6 0 0 0 20 27 1 6 0 0 0 21 28 1 1 0 0 0 22 20 1 6 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.13
Volume:	383.856
LogP:	3.18
LogD:	3.075
LogS:	-4.681
# Rotatable Bonds:	6
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	3.848
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97
MDCK Permeability:	2.073485120490659e-05
Pgp-inhibitor:	0.383
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.768
Plasma Protein Binding (PPB):	94.60285949707031%
Volume Distribution (VD):	1.063
Pgp-substrate:	3.297187328338623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.512
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.42
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.244
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	6.008
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.465
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.885
Carcinogencity:	0.288
Eye Corrosion:	0.023
Eye Irritation:	0.179
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC476033

Natural Product ID:	NPC476033
*Common Name:**	(+)-Crassalactone C
IUPAC Name:	[(R)-[(2S,3S,3aR,6aR)-3-hydroxy-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-2-yl]-phenylmethyl] (E)-3-phenylprop-2-enoate
Synonyms:	(+)-Crassalactone C
Standard InCHIKey:	GDYNBHXFRSGEGM-IBXQNDSPSA-N
Standard InCHI:	InChI=1S/C22H20O6/c23-17(12-11-14-7-3-1-4-8-14)27-20(15-9-5-2-6-10-15)22-19(25)21-16(26-22)13-18(24)28-21/h1-12,16,19-22,25H,13H2/b12-11+/t16-,19-,20-,21+,22+/m1/s1
SMILES:	C1C2C(C(C(O2)C(C3=CC=CC=C3)OC(=O)C=CC4=CC=CC=C4)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522799
PubChem CID:	16097756
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO33115	polyalthia crasa	Species	Annonaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[17190450]

☑ 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
ED50	6
IC50	19

Activity Type	# Activity
Cell Line	22
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[520739]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	25450.0	nM	PMID[520739]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	15460.0	nM	PMID[520739]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11250.0	nM	PMID[520739]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	100000.0	nM	PMID[520739]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[520740]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[520740]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[520740]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[520740]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	3560.0	nM	PMID[520741]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[520741]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	25450.0	nM	PMID[520741]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	15460.0	nM	PMID[520741]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11250.0	nM	PMID[520741]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	100000.0	nM	PMID[520741]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	25450.0	nM	PMID[520742]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	3560.0	nM	PMID[520742]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	15460.0	nM	PMID[520742]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7340.0	nM	PMID[520742]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	87980.0	nM	PMID[520742]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11250.0	nM	PMID[520742]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	100000.0	nM	PMID[520742]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[520740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[520742]

☑ 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 NPC476033 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	267
0.1-0.2	901
0.2-0.3	2360
0.3-0.4	5828
0.4-0.5	10993
0.5-0.6	10883
0.6-0.7	10383
0.7-0.8	1061
0.8-0.85	15
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC79608
0.8908	High Similarity	NPC210531
0.872	High Similarity	NPC138798
0.8485	Intermediate Similarity	NPC136994
0.8485	Intermediate Similarity	NPC88255
0.843	Intermediate Similarity	NPC172525
0.8359	Intermediate Similarity	NPC246166
0.8347	Intermediate Similarity	NPC265002
0.8321	Intermediate Similarity	NPC214246
0.8264	Intermediate Similarity	NPC234376
0.8235	Intermediate Similarity	NPC277788
0.8214	Intermediate Similarity	NPC477737
0.8156	Intermediate Similarity	NPC205389
0.813	Intermediate Similarity	NPC474363
0.813	Intermediate Similarity	NPC87069
0.812	Intermediate Similarity	NPC60825
0.812	Intermediate Similarity	NPC291419
0.8116	Intermediate Similarity	NPC242355
0.8116	Intermediate Similarity	NPC77493
0.8115	Intermediate Similarity	NPC185840
0.8115	Intermediate Similarity	NPC158282
0.8106	Intermediate Similarity	NPC301857
0.8102	Intermediate Similarity	NPC308976
0.8092	Intermediate Similarity	NPC114096
0.8083	Intermediate Similarity	NPC20485
0.8056	Intermediate Similarity	NPC477905
0.8056	Intermediate Similarity	NPC472548
0.8047	Intermediate Similarity	NPC229600
0.8042	Intermediate Similarity	NPC25484
0.8042	Intermediate Similarity	NPC232583
0.803	Intermediate Similarity	NPC148026
0.8015	Intermediate Similarity	NPC200154
0.8015	Intermediate Similarity	NPC477893
0.8015	Intermediate Similarity	NPC477896
0.8014	Intermediate Similarity	NPC25043
0.8014	Intermediate Similarity	NPC134131
0.8	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC472315
0.8	Intermediate Similarity	NPC474376
0.8	Intermediate Similarity	NPC475203
0.8	Intermediate Similarity	NPC37115
0.7986	Intermediate Similarity	NPC471103
0.7971	Intermediate Similarity	NPC473301
0.7958	Intermediate Similarity	NPC210330
0.7958	Intermediate Similarity	NPC469513
0.7958	Intermediate Similarity	NPC170668
0.7955	Intermediate Similarity	NPC472706
0.7945	Intermediate Similarity	NPC472549
0.7926	Intermediate Similarity	NPC108553
0.7926	Intermediate Similarity	NPC318799
0.7926	Intermediate Similarity	NPC233692
0.7926	Intermediate Similarity	NPC239358
0.7923	Intermediate Similarity	NPC223351
0.7923	Intermediate Similarity	NPC472703
0.7914	Intermediate Similarity	NPC100913
0.7914	Intermediate Similarity	NPC275592
0.791	Intermediate Similarity	NPC27712
0.7903	Intermediate Similarity	NPC474176
0.7895	Intermediate Similarity	NPC472707
0.7891	Intermediate Similarity	NPC106895
0.7887	Intermediate Similarity	NPC127857
0.7883	Intermediate Similarity	NPC68517
0.7883	Intermediate Similarity	NPC106406
0.7877	Intermediate Similarity	NPC133430
0.7877	Intermediate Similarity	NPC477098
0.7877	Intermediate Similarity	NPC469477
0.7877	Intermediate Similarity	NPC477100
0.7872	Intermediate Similarity	NPC95449
0.7872	Intermediate Similarity	NPC45307
0.7868	Intermediate Similarity	NPC472248
0.7863	Intermediate Similarity	NPC472704
0.7863	Intermediate Similarity	NPC471466
0.7862	Intermediate Similarity	NPC51602
0.7857	Intermediate Similarity	NPC87448
0.7857	Intermediate Similarity	NPC473497
0.7857	Intermediate Similarity	NPC27377
0.7857	Intermediate Similarity	NPC118080
0.7857	Intermediate Similarity	NPC187566
0.7857	Intermediate Similarity	NPC213567
0.7857	Intermediate Similarity	NPC97947
0.7857	Intermediate Similarity	NPC472576
0.7857	Intermediate Similarity	NPC41481
0.7857	Intermediate Similarity	NPC475413
0.7857	Intermediate Similarity	NPC291599
0.7857	Intermediate Similarity	NPC474303
0.7852	Intermediate Similarity	NPC17567
0.7851	Intermediate Similarity	NPC136962
0.7847	Intermediate Similarity	NPC60509
0.7847	Intermediate Similarity	NPC250046
0.7847	Intermediate Similarity	NPC81698
0.7847	Intermediate Similarity	NPC229264
0.784	Intermediate Similarity	NPC307651
0.7838	Intermediate Similarity	NPC469417
0.7838	Intermediate Similarity	NPC181924
0.7833	Intermediate Similarity	NPC280616
0.7833	Intermediate Similarity	NPC171831
0.7833	Intermediate Similarity	NPC242913
0.7832	Intermediate Similarity	NPC223185
0.7826	Intermediate Similarity	NPC182217
0.7826	Intermediate Similarity	NPC233350
0.7826	Intermediate Similarity	NPC70680
0.7823	Intermediate Similarity	NPC282239
0.7823	Intermediate Similarity	NPC473670
0.7823	Intermediate Similarity	NPC21410
0.7817	Intermediate Similarity	NPC470152
0.7817	Intermediate Similarity	NPC478250
0.7817	Intermediate Similarity	NPC475122
0.7817	Intermediate Similarity	NPC241951
0.7817	Intermediate Similarity	NPC475759
0.781	Intermediate Similarity	NPC28836
0.781	Intermediate Similarity	NPC311492
0.781	Intermediate Similarity	NPC153617
0.7801	Intermediate Similarity	NPC182869
0.7795	Intermediate Similarity	NPC190298
0.7794	Intermediate Similarity	NPC469499
0.7794	Intermediate Similarity	NPC233860
0.7793	Intermediate Similarity	NPC471076
0.7793	Intermediate Similarity	NPC192568
0.7793	Intermediate Similarity	NPC91730
0.7793	Intermediate Similarity	NPC165260
0.7793	Intermediate Similarity	NPC161239
0.7793	Intermediate Similarity	NPC198455
0.7793	Intermediate Similarity	NPC7095
0.7786	Intermediate Similarity	NPC171207
0.7786	Intermediate Similarity	NPC472547
0.7786	Intermediate Similarity	NPC97667
0.7786	Intermediate Similarity	NPC24295
0.7786	Intermediate Similarity	NPC90614
0.7786	Intermediate Similarity	NPC283560
0.7785	Intermediate Similarity	NPC469399
0.7785	Intermediate Similarity	NPC49297
0.7778	Intermediate Similarity	NPC30890
0.777	Intermediate Similarity	NPC217091
0.777	Intermediate Similarity	NPC39549
0.7769	Intermediate Similarity	NPC269457
0.7762	Intermediate Similarity	NPC469349
0.7762	Intermediate Similarity	NPC472568
0.7762	Intermediate Similarity	NPC96903
0.7762	Intermediate Similarity	NPC171525
0.7762	Intermediate Similarity	NPC473088
0.7762	Intermediate Similarity	NPC177940
0.7762	Intermediate Similarity	NPC472572
0.7762	Intermediate Similarity	NPC476973
0.7762	Intermediate Similarity	NPC70403
0.7762	Intermediate Similarity	NPC158663
0.7762	Intermediate Similarity	NPC184817
0.7762	Intermediate Similarity	NPC277053
0.7762	Intermediate Similarity	NPC472575
0.7762	Intermediate Similarity	NPC470159
0.7762	Intermediate Similarity	NPC200471
0.7762	Intermediate Similarity	NPC174982
0.7762	Intermediate Similarity	NPC470157
0.7762	Intermediate Similarity	NPC29704
0.7762	Intermediate Similarity	NPC472571
0.7762	Intermediate Similarity	NPC301946
0.7762	Intermediate Similarity	NPC471104
0.7755	Intermediate Similarity	NPC242262
0.7755	Intermediate Similarity	NPC473414
0.7755	Intermediate Similarity	NPC237549
0.7755	Intermediate Similarity	NPC256142
0.7755	Intermediate Similarity	NPC472030
0.7755	Intermediate Similarity	NPC1173
0.7755	Intermediate Similarity	NPC249471
0.7755	Intermediate Similarity	NPC304876
0.7755	Intermediate Similarity	NPC472005
0.7755	Intermediate Similarity	NPC472022
0.7755	Intermediate Similarity	NPC257213
0.7755	Intermediate Similarity	NPC146310
0.7755	Intermediate Similarity	NPC158333
0.7755	Intermediate Similarity	NPC265395
0.7754	Intermediate Similarity	NPC474895
0.775	Intermediate Similarity	NPC234305
0.7748	Intermediate Similarity	NPC275477
0.7746	Intermediate Similarity	NPC163087
0.7746	Intermediate Similarity	NPC82467
0.7746	Intermediate Similarity	NPC477894
0.774	Intermediate Similarity	NPC470153
0.774	Intermediate Similarity	NPC197037
0.773	Intermediate Similarity	NPC179505
0.773	Intermediate Similarity	NPC156709
0.773	Intermediate Similarity	NPC16912
0.7721	Intermediate Similarity	NPC319995
0.7721	Intermediate Similarity	NPC289415
0.7718	Intermediate Similarity	NPC477735
0.7718	Intermediate Similarity	NPC472393
0.7717	Intermediate Similarity	NPC471616
0.7717	Intermediate Similarity	NPC149691
0.7714	Intermediate Similarity	NPC9905
0.7708	Intermediate Similarity	NPC475528
0.7708	Intermediate Similarity	NPC240115
0.7703	Intermediate Similarity	NPC228204
0.7703	Intermediate Similarity	NPC26033
0.7703	Intermediate Similarity	NPC251139
0.7703	Intermediate Similarity	NPC114410
0.7703	Intermediate Similarity	NPC112523
0.7698	Intermediate Similarity	NPC472551
0.7698	Intermediate Similarity	NPC472545
0.7697	Intermediate Similarity	NPC66193
0.7697	Intermediate Similarity	NPC239818
0.7697	Intermediate Similarity	NPC218471

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 NPC476033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	618
0.2-0.3	1453
0.3-0.4	2808
0.4-0.5	2471
0.5-0.6	1202
0.6-0.7	364
0.7-0.8	15
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
0.8134	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5048	Discontinued
0.782	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6190	Approved
0.7557	Intermediate Similarity	NPD5126	Approved
0.7557	Intermediate Similarity	NPD5125	Phase 3
0.752	Intermediate Similarity	NPD2067	Discontinued
0.7518	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2629	Approved
0.7402	Intermediate Similarity	NPD969	Suspended
0.7394	Intermediate Similarity	NPD7033	Discontinued
0.7355	Intermediate Similarity	NPD1238	Approved
0.7338	Intermediate Similarity	NPD3764	Approved
0.7302	Intermediate Similarity	NPD2182	Approved
0.7297	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.7255	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6799	Approved
0.723	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4198	Discontinued
0.7143	Intermediate Similarity	NPD9545	Approved
0.7131	Intermediate Similarity	NPD9495	Approved
0.712	Intermediate Similarity	NPD1237	Approved
0.7115	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7075	Discontinued
0.7097	Intermediate Similarity	NPD5402	Approved
0.7092	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2313	Discontinued
0.7086	Intermediate Similarity	NPD5403	Approved
0.7081	Intermediate Similarity	NPD3818	Discontinued
0.7081	Intermediate Similarity	NPD7799	Discontinued
0.7078	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD7798	Approved
0.7067	Intermediate Similarity	NPD5401	Approved
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7051	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6085	Phase 2
0.7047	Intermediate Similarity	NPD7236	Approved
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.704	Intermediate Similarity	NPD6647	Phase 2
0.7027	Intermediate Similarity	NPD2575	Approved
0.7023	Intermediate Similarity	NPD6010	Discontinued
0.7008	Intermediate Similarity	NPD6685	Approved
0.7007	Intermediate Similarity	NPD1608	Approved
0.6984	Remote Similarity	NPD164	Approved
0.6984	Remote Similarity	NPD5909	Discontinued
0.6972	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4965	Approved
0.6943	Remote Similarity	NPD3882	Suspended
0.6943	Remote Similarity	NPD4967	Phase 2
0.6943	Remote Similarity	NPD4966	Approved
0.6939	Remote Similarity	NPD7266	Discontinued
0.6934	Remote Similarity	NPD6287	Discontinued
0.6929	Remote Similarity	NPD5647	Approved
0.6918	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD8434	Phase 2
0.6905	Remote Similarity	NPD5765	Approved
0.6901	Remote Similarity	NPD7008	Discontinued
0.6892	Remote Similarity	NPD1549	Phase 2
0.6886	Remote Similarity	NPD8407	Phase 2
0.6879	Remote Similarity	NPD5204	Approved
0.6879	Remote Similarity	NPD3817	Phase 2
0.6875	Remote Similarity	NPD6309	Approved
0.6875	Remote Similarity	NPD6311	Approved
0.6875	Remote Similarity	NPD6310	Approved
0.6871	Remote Similarity	NPD2796	Approved
0.6871	Remote Similarity	NPD2935	Discontinued
0.6871	Remote Similarity	NPD1551	Phase 2
0.6866	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4135	Approved
0.6861	Remote Similarity	NPD4136	Approved
0.6861	Remote Similarity	NPD4106	Approved
0.6859	Remote Similarity	NPD1934	Approved
0.6855	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD2532	Approved
0.6842	Remote Similarity	NPD2534	Approved
0.6842	Remote Similarity	NPD2533	Approved
0.6831	Remote Similarity	NPD6832	Phase 2
0.6831	Remote Similarity	NPD2613	Approved
0.6824	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7239	Suspended
0.6815	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7819	Suspended
0.6807	Remote Similarity	NPD8368	Discontinued
0.6806	Remote Similarity	NPD4062	Phase 3
0.6803	Remote Similarity	NPD1202	Approved
0.6803	Remote Similarity	NPD2799	Discontinued
0.68	Remote Similarity	NPD2066	Phase 3
0.68	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7411	Suspended
0.6788	Remote Similarity	NPD5306	Approved
0.6788	Remote Similarity	NPD5305	Approved
0.6788	Remote Similarity	NPD17	Approved
0.6781	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1929	Approved
0.6772	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1930	Approved
0.6772	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7199	Phase 2
0.6769	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7741	Discontinued
0.6765	Remote Similarity	NPD1894	Discontinued
0.6759	Remote Similarity	NPD1240	Approved
0.6757	Remote Similarity	NPD7137	Phase 2
0.6753	Remote Similarity	NPD920	Approved
0.6753	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD37	Approved
0.6746	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6912	Phase 3
0.6741	Remote Similarity	NPD9493	Approved
0.6738	Remote Similarity	NPD2627	Approved
0.6738	Remote Similarity	NPD2159	Approved
0.6738	Remote Similarity	NPD2160	Approved
0.6738	Remote Similarity	NPD2626	Approved
0.6738	Remote Similarity	NPD2625	Approved
0.6738	Remote Similarity	NPD2797	Approved
0.6738	Remote Similarity	NPD2628	Approved
0.6738	Remote Similarity	NPD1203	Approved
0.6736	Remote Similarity	NPD3268	Approved
0.6735	Remote Similarity	NPD2567	Approved
0.6735	Remote Similarity	NPD2569	Approved
0.6732	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5951	Approved
0.6715	Remote Similarity	NPD4102	Approved
0.6715	Remote Similarity	NPD4105	Approved
0.6711	Remote Similarity	NPD2346	Discontinued
0.6709	Remote Similarity	NPD2801	Approved
0.6709	Remote Similarity	NPD8455	Phase 2
0.6708	Remote Similarity	NPD5494	Approved
0.6707	Remote Similarity	NPD6559	Discontinued
0.6706	Remote Similarity	NPD8150	Discontinued
0.6694	Remote Similarity	NPD1989	Approved
0.6693	Remote Similarity	NPD1932	Approved
0.6691	Remote Similarity	NPD4807	Approved
0.6691	Remote Similarity	NPD4806	Approved
0.669	Remote Similarity	NPD2573	Approved
0.669	Remote Similarity	NPD3090	Approved
0.669	Remote Similarity	NPD3089	Approved
0.669	Remote Similarity	NPD3614	Approved
0.669	Remote Similarity	NPD2574	Discontinued
0.669	Remote Similarity	NPD3616	Approved
0.669	Remote Similarity	NPD3615	Approved
0.669	Remote Similarity	NPD4746	Phase 3
0.669	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4404	Approved
0.669	Remote Similarity	NPD2571	Approved
0.669	Remote Similarity	NPD2570	Approved
0.669	Remote Similarity	NPD3087	Approved
0.669	Remote Similarity	NPD3088	Approved
0.669	Remote Similarity	NPD2566	Approved
0.669	Remote Similarity	NPD4745	Approved
0.6689	Remote Similarity	NPD7305	Phase 1
0.6687	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5958	Discontinued
0.6667	Remote Similarity	NPD5667	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6166	Phase 2
0.6646	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD943	Approved
0.6643	Remote Similarity	NPD3661	Approved
0.6643	Remote Similarity	NPD3663	Approved
0.6643	Remote Similarity	NPD3664	Approved
0.6643	Remote Similarity	NPD3662	Phase 3
0.6628	Remote Similarity	NPD8361	Approved
0.6628	Remote Similarity	NPD8435	Approved
0.6628	Remote Similarity	NPD8360	Approved
0.6627	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8312	Approved
0.6627	Remote Similarity	NPD5844	Phase 1
0.6627	Remote Similarity	NPD8313	Approved
0.6626	Remote Similarity	NPD3787	Discontinued
0.6626	Remote Similarity	NPD6232	Discontinued
0.6621	Remote Similarity	NPD1699	Clinical (unspecified phase)

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