NPASS Compound

Structure

NPC90431 OpenBabel07101718292D 26 28 0 0 1 0 0 0 0 0999 V2000 2.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7859 4.8126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0917 5.1727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5780 3.8344 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 14 7 1 6 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	3.104
LogD:	3.32
LogS:	-3.874
# Rotatable Bonds:	5
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	2.993
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.861
MDCK Permeability:	1.843947211455088e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.092
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	98.5262680053711%
Volume Distribution (VD):	0.48
Pgp-substrate:	3.5446584224700928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.215
CYP2C9-inhibitor:	0.817
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.742
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	13.881
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.643
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.83
Carcinogencity:	0.857
Eye Corrosion:	0.007
Eye Irritation:	0.877
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC90431

Natural Product ID:	NPC90431
*Common Name:**	Acutissimalignan B
IUPAC Name:	(3E,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methylidene]oxolan-2-one
Synonyms:	acutissimalignan B
Standard InCHIKey:	RJVKWKAOIHNOQD-VLHYRRCOSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,8-10,14,21-22H,7,11H2,1-2H3/b15-8+/t14-/m1/s1
SMILES:	COc1cc(ccc1O)C[C@@H]1COC(=O)/C/1=C/c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460247
PubChem CID:	24862533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO33358	phyllanthus acutissima	Species	n.a.	Eukaryota	aerial parts	n.a.	n.a.	PMID[18271551]

☑ 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
EC50	1
ED50	6
IC50	1
Others	2

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	45.4	%	PMID[478452]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[478452]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[478452]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[478452]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[478452]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[478452]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Ratio IC50/EC50	=	4.9	n.a.	PMID[478452]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	9.9	ug.mL-1	PMID[478452]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	48.2	ug.mL-1	PMID[478452]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[478452]

☑ 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 NPC90431 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	281
0.1-0.2	1201
0.2-0.3	2879
0.3-0.4	6929
0.4-0.5	11425
0.5-0.6	4126
0.6-0.7	9582
0.7-0.8	5589
0.8-0.85	508
0.85-0.9	152
0.9-0.95	17
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC300776
0.9692	High Similarity	NPC176814
0.9692	High Similarity	NPC5310
0.9692	High Similarity	NPC4982
0.9692	High Similarity	NPC68779
0.9265	High Similarity	NPC282291
0.9265	High Similarity	NPC29599
0.9265	High Similarity	NPC166137
0.9265	High Similarity	NPC100675
0.9225	High Similarity	NPC213552
0.9225	High Similarity	NPC120225
0.9197	High Similarity	NPC253722
0.9197	High Similarity	NPC31751
0.9197	High Similarity	NPC253481
0.9179	High Similarity	NPC113295
0.916	High Similarity	NPC304622
0.916	High Similarity	NPC241354
0.9154	High Similarity	NPC123722
0.9154	High Similarity	NPC5018
0.9154	High Similarity	NPC276466
0.9154	High Similarity	NPC223807
0.9154	High Similarity	NPC123228
0.9154	High Similarity	NPC151167
0.9147	High Similarity	NPC280767
0.9147	High Similarity	NPC289459
0.913	High Similarity	NPC273657
0.913	High Similarity	NPC106920
0.9118	High Similarity	NPC284409
0.9077	High Similarity	NPC90128
0.9077	High Similarity	NPC84076
0.9077	High Similarity	NPC179777
0.9077	High Similarity	NPC303680
0.907	High Similarity	NPC246704
0.9058	High Similarity	NPC52664
0.9051	High Similarity	NPC288452
0.9051	High Similarity	NPC289690
0.903	High Similarity	NPC475468
0.9015	High Similarity	NPC83062
0.9	High Similarity	NPC257589
0.9	High Similarity	NPC53884
0.9	High Similarity	NPC258671
0.9	High Similarity	NPC53305
0.9	High Similarity	NPC223185
0.8993	High Similarity	NPC470811
0.8993	High Similarity	NPC477696
0.8993	High Similarity	NPC477697
0.8963	High Similarity	NPC471110
0.8958	High Similarity	NPC476434
0.8951	High Similarity	NPC261322
0.8939	High Similarity	NPC226661
0.8931	High Similarity	NPC127937
0.8931	High Similarity	NPC92207
0.8929	High Similarity	NPC304956
0.8929	High Similarity	NPC46880
0.8923	High Similarity	NPC146886
0.8923	High Similarity	NPC20443
0.8923	High Similarity	NPC60517
0.8905	High Similarity	NPC281780
0.8889	High Similarity	NPC327410
0.8889	High Similarity	NPC243891
0.8889	High Similarity	NPC32079
0.8881	High Similarity	NPC318799
0.8873	High Similarity	NPC221383
0.8873	High Similarity	NPC283081
0.8873	High Similarity	NPC299090
0.8873	High Similarity	NPC143892
0.8849	High Similarity	NPC82336
0.8849	High Similarity	NPC78987
0.8846	High Similarity	NPC31344
0.8846	High Similarity	NPC4181
0.8846	High Similarity	NPC317769
0.8846	High Similarity	NPC164778
0.8846	High Similarity	NPC257976
0.8846	High Similarity	NPC242372
0.8837	High Similarity	NPC194416
0.8837	High Similarity	NPC177291
0.8837	High Similarity	NPC70752
0.8832	High Similarity	NPC230968
0.8832	High Similarity	NPC102260
0.8832	High Similarity	NPC120852
0.8828	High Similarity	NPC267091
0.8824	High Similarity	NPC67247
0.8815	High Similarity	NPC239302
0.8811	High Similarity	NPC1580
0.8806	High Similarity	NPC215941
0.8806	High Similarity	NPC65935
0.8806	High Similarity	NPC172673
0.8806	High Similarity	NPC123196
0.8806	High Similarity	NPC319282
0.8806	High Similarity	NPC275724
0.8806	High Similarity	NPC311419
0.8806	High Similarity	NPC137427
0.8806	High Similarity	NPC244246
0.8797	High Similarity	NPC110313
0.8797	High Similarity	NPC478215
0.8788	High Similarity	NPC276014
0.8786	High Similarity	NPC67467
0.8779	High Similarity	NPC288945
0.8779	High Similarity	NPC312404
0.8779	High Similarity	NPC273686
0.8777	High Similarity	NPC147379
0.8769	High Similarity	NPC114298
0.876	High Similarity	NPC204466
0.8759	High Similarity	NPC477301
0.8759	High Similarity	NPC204592
0.8759	High Similarity	NPC477700
0.875	High Similarity	NPC216223
0.875	High Similarity	NPC205915
0.875	High Similarity	NPC145569
0.8714	High Similarity	NPC326065
0.8714	High Similarity	NPC28398
0.8712	High Similarity	NPC3221
0.8702	High Similarity	NPC160900
0.8702	High Similarity	NPC106659
0.8702	High Similarity	NPC18984
0.8702	High Similarity	NPC163083
0.8702	High Similarity	NPC229084
0.8696	High Similarity	NPC471988
0.8692	High Similarity	NPC201777
0.8686	High Similarity	NPC135127
0.8682	High Similarity	NPC202474
0.8681	High Similarity	NPC98009
0.8681	High Similarity	NPC236166
0.8681	High Similarity	NPC472969
0.8667	High Similarity	NPC66905
0.8662	High Similarity	NPC160378
0.8662	High Similarity	NPC239608
0.8662	High Similarity	NPC46161
0.8662	High Similarity	NPC473090
0.8662	High Similarity	NPC469615
0.8643	High Similarity	NPC322021
0.8643	High Similarity	NPC106055
0.8643	High Similarity	NPC110699
0.8643	High Similarity	NPC474784
0.8639	High Similarity	NPC44730
0.8623	High Similarity	NPC211386
0.8623	High Similarity	NPC470990
0.8621	High Similarity	NPC477695
0.8621	High Similarity	NPC474965
0.8621	High Similarity	NPC476394
0.8621	High Similarity	NPC125570
0.8621	High Similarity	NPC55327
0.8621	High Similarity	NPC668
0.8621	High Similarity	NPC293757
0.8621	High Similarity	NPC98809
0.8621	High Similarity	NPC174512
0.8615	High Similarity	NPC470848
0.8615	High Similarity	NPC60962
0.8615	High Similarity	NPC470849
0.8615	High Similarity	NPC109083
0.8615	High Similarity	NPC189844
0.8615	High Similarity	NPC224814
0.8615	High Similarity	NPC269843
0.8615	High Similarity	NPC14007
0.8615	High Similarity	NPC158949
0.8613	High Similarity	NPC155209
0.8613	High Similarity	NPC168799
0.8605	High Similarity	NPC263386
0.8605	High Similarity	NPC141791
0.8603	High Similarity	NPC198388
0.8601	High Similarity	NPC469683
0.8601	High Similarity	NPC163898
0.8592	High Similarity	NPC169214
0.8592	High Similarity	NPC176030
0.8592	High Similarity	NPC229218
0.8592	High Similarity	NPC141817
0.8592	High Similarity	NPC192597
0.8582	High Similarity	NPC20404
0.8582	High Similarity	NPC293641
0.8582	High Similarity	NPC20287
0.8582	High Similarity	NPC9218
0.8582	High Similarity	NPC12022
0.8571	High Similarity	NPC132723
0.8571	High Similarity	NPC95498
0.8571	High Similarity	NPC76032
0.8571	High Similarity	NPC87113
0.8571	High Similarity	NPC246566
0.8551	High Similarity	NPC144662
0.8551	High Similarity	NPC106406
0.8551	High Similarity	NPC110958
0.8551	High Similarity	NPC19890
0.8542	High Similarity	NPC98356
0.854	High Similarity	NPC61
0.854	High Similarity	NPC111888
0.854	High Similarity	NPC5419
0.854	High Similarity	NPC25581
0.854	High Similarity	NPC18074
0.8538	High Similarity	NPC117780
0.8538	High Similarity	NPC2058
0.8538	High Similarity	NPC227217
0.8538	High Similarity	NPC232316
0.8538	High Similarity	NPC95614
0.8538	High Similarity	NPC56214
0.8538	High Similarity	NPC165133
0.8538	High Similarity	NPC242885
0.8529	High Similarity	NPC275950
0.8529	High Similarity	NPC181079
0.8529	High Similarity	NPC173308
0.8527	High Similarity	NPC137537
0.8527	High Similarity	NPC277460

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 NPC90431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	776
0.2-0.3	1429
0.3-0.4	2360
0.4-0.5	2220
0.5-0.6	1223
0.6-0.7	740
0.7-0.8	159
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8702	High Similarity	NPD4379	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD9494	Approved
0.8264	Intermediate Similarity	NPD4110	Phase 3
0.8264	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6355	Discontinued
0.8168	Intermediate Similarity	NPD5536	Phase 2
0.8138	Intermediate Similarity	NPD8166	Discontinued
0.8117	Intermediate Similarity	NPD6234	Discontinued
0.8105	Intermediate Similarity	NPD3882	Suspended
0.8014	Intermediate Similarity	NPD4628	Phase 3
0.8014	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD5283	Phase 1
0.8	Intermediate Similarity	NPD6798	Discontinued
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7984	Intermediate Similarity	NPD228	Approved
0.7959	Intermediate Similarity	NPD6190	Approved
0.7929	Intermediate Similarity	NPD3027	Phase 3
0.7908	Intermediate Similarity	NPD37	Approved
0.7871	Intermediate Similarity	NPD4965	Approved
0.7871	Intermediate Similarity	NPD4966	Approved
0.7871	Intermediate Similarity	NPD4967	Phase 2
0.7832	Intermediate Similarity	NPD230	Phase 1
0.7832	Intermediate Similarity	NPD447	Suspended
0.7829	Intermediate Similarity	NPD3455	Phase 2
0.7826	Intermediate Similarity	NPD1283	Approved
0.7818	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6233	Phase 2
0.7817	Intermediate Similarity	NPD4062	Phase 3
0.7815	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7095	Approved
0.7793	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD1934	Approved
0.777	Intermediate Similarity	NPD2797	Approved
0.7764	Intermediate Similarity	NPD7228	Approved
0.7764	Intermediate Similarity	NPD3818	Discontinued
0.7746	Intermediate Similarity	NPD3764	Approved
0.7742	Intermediate Similarity	NPD2801	Approved
0.7704	Intermediate Similarity	NPD1894	Discontinued
0.7692	Intermediate Similarity	NPD3022	Approved
0.7692	Intermediate Similarity	NPD3021	Approved
0.7687	Intermediate Similarity	NPD7266	Discontinued
0.7683	Intermediate Similarity	NPD7685	Pre-registration
0.7681	Intermediate Similarity	NPD1608	Approved
0.7674	Intermediate Similarity	NPD1358	Approved
0.7673	Intermediate Similarity	NPD8127	Discontinued
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7664	Intermediate Similarity	NPD3847	Discontinued
0.7662	Intermediate Similarity	NPD7028	Phase 2
0.7639	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3620	Phase 2
0.7639	Intermediate Similarity	NPD2979	Phase 3
0.7635	Intermediate Similarity	NPD5958	Discontinued
0.7632	Intermediate Similarity	NPD6273	Approved
0.7628	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3268	Approved
0.7619	Intermediate Similarity	NPD2438	Suspended
0.7613	Intermediate Similarity	NPD6385	Approved
0.7613	Intermediate Similarity	NPD6386	Approved
0.7609	Intermediate Similarity	NPD1281	Approved
0.7609	Intermediate Similarity	NPD1535	Discovery
0.7597	Intermediate Similarity	NPD3134	Approved
0.7589	Intermediate Similarity	NPD5647	Approved
0.7584	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3817	Phase 2
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1481	Phase 2
0.7534	Intermediate Similarity	NPD6653	Approved
0.7518	Intermediate Similarity	NPD1357	Approved
0.7518	Intermediate Similarity	NPD5585	Approved
0.7517	Intermediate Similarity	NPD825	Approved
0.7517	Intermediate Similarity	NPD826	Approved
0.7517	Intermediate Similarity	NPD4534	Discontinued
0.7516	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6232	Discontinued
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6873	Phase 2
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7466	Intermediate Similarity	NPD1933	Approved
0.7464	Intermediate Similarity	NPD17	Approved
0.7464	Intermediate Similarity	NPD4626	Approved
0.7463	Intermediate Similarity	NPD1241	Discontinued
0.745	Intermediate Similarity	NPD2344	Approved
0.7447	Intermediate Similarity	NPD1876	Approved
0.7445	Intermediate Similarity	NPD9545	Approved
0.744	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6166	Phase 2
0.7417	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1613	Approved
0.7397	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1203	Approved
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7391	Intermediate Similarity	NPD5494	Approved
0.7391	Intermediate Similarity	NPD1651	Approved
0.7391	Intermediate Similarity	NPD5691	Approved
0.7388	Intermediate Similarity	NPD5535	Approved
0.7386	Intermediate Similarity	NPD4357	Discontinued
0.7386	Intermediate Similarity	NPD6799	Approved
0.7386	Intermediate Similarity	NPD1511	Approved
0.7383	Intermediate Similarity	NPD6032	Approved
0.7383	Intermediate Similarity	NPD2531	Phase 2
0.7379	Intermediate Similarity	NPD2313	Discontinued
0.7375	Intermediate Similarity	NPD7075	Discontinued
0.7368	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2354	Approved
0.7365	Intermediate Similarity	NPD7097	Phase 1
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7361	Intermediate Similarity	NPD2614	Approved
0.7361	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3705	Approved
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7348	Intermediate Similarity	NPD2684	Approved
0.7343	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD6663	Approved
0.7329	Intermediate Similarity	NPD8032	Phase 2
0.7321	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD1653	Approved
0.7305	Intermediate Similarity	NPD3972	Approved
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5736	Approved
0.729	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD7054	Approved
0.7285	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD3267	Approved
0.7273	Intermediate Similarity	NPD3266	Approved
0.7267	Intermediate Similarity	NPD4476	Approved
0.7267	Intermediate Similarity	NPD4477	Approved
0.7262	Intermediate Similarity	NPD7240	Approved
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7843	Approved
0.7256	Intermediate Similarity	NPD5242	Approved
0.7255	Intermediate Similarity	NPD2309	Approved
0.7255	Intermediate Similarity	NPD3887	Approved
0.7254	Intermediate Similarity	NPD4359	Approved
0.7254	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7472	Approved
0.7239	Intermediate Similarity	NPD2821	Approved
0.723	Intermediate Similarity	NPD4340	Discontinued
0.723	Intermediate Similarity	NPD555	Phase 2
0.723	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD7157	Approved
0.7226	Intermediate Similarity	NPD2532	Approved
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2534	Approved
0.7222	Intermediate Similarity	NPD257	Approved
0.7222	Intermediate Similarity	NPD258	Approved
0.7222	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD6599	Discontinued
0.7214	Intermediate Similarity	NPD1778	Approved
0.7208	Intermediate Similarity	NPD7440	Discontinued
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD7033	Discontinued
0.7197	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7183	Intermediate Similarity	NPD9717	Approved
0.7183	Intermediate Similarity	NPD9269	Phase 2
0.7179	Intermediate Similarity	NPD5049	Phase 3
0.7172	Intermediate Similarity	NPD2861	Phase 2
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD1558	Phase 1
0.716	Intermediate Similarity	NPD7039	Approved
0.716	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7038	Approved
0.7153	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2629	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7152	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD824	Approved
0.7143	Intermediate Similarity	NPD5977	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD5978	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7125	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD3146	Approved
0.7115	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6002	Phase 3
0.7105	Intermediate Similarity	NPD6005	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