NPASS Compound

Structure

NPC249791 OpenBabel07101719522D 28 29 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 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 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 22 2 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 23 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 13 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	395.099
LogP:	1.754
LogD:	2.074
LogS:	-3.593
# Rotatable Bonds:	10
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	3.382
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	7.074281256791437e-06
Pgp-inhibitor:	0.269
Pgp-substrate:	0.678
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.896
Plasma Protein Binding (PPB):	92.3637924194336%
Volume Distribution (VD):	0.599
Pgp-substrate:	6.979910850524902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.662
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.57

ADMET: Excretion

Clearance (CL):	7.664
Half-life (T1/2):	0.738

ADMET: Toxicity

hERG Blockers:	0.213
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.243
AMES Toxicity:	0.454
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.514
Carcinogencity:	0.687
Eye Corrosion:	0.003
Eye Irritation:	0.094
Respiratory Toxicity:	0.474

Download Data

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

Natural Product: NPC249791

Natural Product ID:	NPC249791
*Common Name:**	Pinnatifidanin B Viii
IUPAC Name:	(E)-3-[4-[(1R,2R)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-yl]oxy-3-methoxyphenyl]prop-2-enal
Synonyms:
Standard InCHIKey:	FFSBZOPEPNMMNU-QLAYCGNHSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-25-18-12-15(7-8-16(18)24)21(27-3)20(13-23)28-17-9-6-14(5-4-10-22)11-19(17)26-2/h4-12,20-21,23-24H,13H2,1-3H3/b5-4+/t20-,21-/m1/s1
SMILES:	O=C/C=C/c1ccc(c(c1)OC)O[C@@H]([C@@H](c1ccc(c(c1)OC)O)OC)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2430309
PubChem CID:	49788702
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15739361]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[23845552]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23999046]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	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	11

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	50000.0	nM	PMID[496541]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[496541]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	2710.0	nM	PMID[496541]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25460.0	nM	PMID[496541]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	31930.0	nM	PMID[496541]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[496541]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	26350.0	nM	PMID[496541]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	39970.0	nM	PMID[496541]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[496541]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[496541]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[496541]

☑ 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 NPC249791 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	319
0.1-0.2	1407
0.2-0.3	4274
0.3-0.4	10751
0.4-0.5	7512
0.5-0.6	3607
0.6-0.7	7762
0.7-0.8	5811
0.8-0.85	898
0.85-0.9	282
0.9-0.95	62
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119060
1.0	High Similarity	NPC237594
1.0	High Similarity	NPC476387
0.9767	High Similarity	NPC214729
0.9621	High Similarity	NPC267291
0.9549	High Similarity	NPC224876
0.9549	High Similarity	NPC83375
0.9478	High Similarity	NPC278469
0.9478	High Similarity	NPC193722
0.947	High Similarity	NPC126206
0.9449	High Similarity	NPC292056
0.9449	High Similarity	NPC111247
0.9449	High Similarity	NPC118787
0.9449	High Similarity	NPC183181
0.9449	High Similarity	NPC147821
0.9449	High Similarity	NPC319625
0.9449	High Similarity	NPC41706
0.9449	High Similarity	NPC163332
0.9394	High Similarity	NPC471665
0.9394	High Similarity	NPC471664
0.9389	High Similarity	NPC135127
0.937	High Similarity	NPC191037
0.937	High Similarity	NPC58607
0.937	High Similarity	NPC178284
0.9338	High Similarity	NPC93433
0.9338	High Similarity	NPC284881
0.9338	High Similarity	NPC474444
0.9338	High Similarity	NPC264706
0.9313	High Similarity	NPC36490
0.9302	High Similarity	NPC5851
0.9302	High Similarity	NPC86030
0.9291	High Similarity	NPC194519
0.9291	High Similarity	NPC87113
0.9225	High Similarity	NPC72529
0.9213	High Similarity	NPC114901
0.9213	High Similarity	NPC293701
0.9213	High Similarity	NPC48990
0.9213	High Similarity	NPC109822
0.9213	High Similarity	NPC94276
0.9203	High Similarity	NPC9370
0.9203	High Similarity	NPC287495
0.916	High Similarity	NPC472597
0.9091	High Similarity	NPC160991
0.9091	High Similarity	NPC184447
0.9091	High Similarity	NPC16208
0.9091	High Similarity	NPC35932
0.9091	High Similarity	NPC7903
0.9084	High Similarity	NPC472338
0.9077	High Similarity	NPC252307
0.9077	High Similarity	NPC245826
0.9077	High Similarity	NPC474178
0.9071	High Similarity	NPC473408
0.9055	High Similarity	NPC71090
0.9008	High Similarity	NPC210623
0.9008	High Similarity	NPC190629
0.9008	High Similarity	NPC273295
0.9008	High Similarity	NPC285339
0.9008	High Similarity	NPC226788
0.9008	High Similarity	NPC470258
0.9008	High Similarity	NPC222004
0.9008	High Similarity	NPC3439
0.9008	High Similarity	NPC202582
0.9008	High Similarity	NPC218856
0.9	High Similarity	NPC165045
0.9	High Similarity	NPC118533
0.8993	High Similarity	NPC473909
0.8993	High Similarity	NPC274960
0.8993	High Similarity	NPC143120
0.8993	High Similarity	NPC163898
0.8986	High Similarity	NPC478239
0.8984	High Similarity	NPC471693
0.8976	High Similarity	NPC470804
0.8955	High Similarity	NPC170694
0.8955	High Similarity	NPC310854
0.8947	High Similarity	NPC470752
0.8939	High Similarity	NPC187998
0.8939	High Similarity	NPC77040
0.8939	High Similarity	NPC42300
0.8939	High Similarity	NPC174495
0.8939	High Similarity	NPC257582
0.8939	High Similarity	NPC145305
0.8939	High Similarity	NPC153739
0.8939	High Similarity	NPC92164
0.8939	High Similarity	NPC241522
0.8939	High Similarity	NPC242807
0.8939	High Similarity	NPC64201
0.8936	High Similarity	NPC236166
0.8923	High Similarity	NPC213552
0.8923	High Similarity	NPC120225
0.8913	High Similarity	NPC157816
0.8913	High Similarity	NPC140502
0.8889	High Similarity	NPC472337
0.8889	High Similarity	NPC55040
0.8881	High Similarity	NPC475840
0.8872	High Similarity	NPC277804
0.8872	High Similarity	NPC469613
0.8872	High Similarity	NPC470095
0.8872	High Similarity	NPC309787
0.8872	High Similarity	NPC470096
0.8872	High Similarity	NPC469625
0.8872	High Similarity	NPC30043
0.8865	High Similarity	NPC476347
0.8864	High Similarity	NPC476968
0.8864	High Similarity	NPC475875
0.8864	High Similarity	NPC170844
0.8855	High Similarity	NPC474119
0.8855	High Similarity	NPC210355
0.8855	High Similarity	NPC5428
0.8846	High Similarity	NPC289459
0.8846	High Similarity	NPC148627
0.8841	High Similarity	NPC186406
0.8832	High Similarity	NPC100389
0.8828	High Similarity	NPC54872
0.8828	High Similarity	NPC312675
0.8828	High Similarity	NPC290451
0.8828	High Similarity	NPC113865
0.8828	High Similarity	NPC324571
0.8828	High Similarity	NPC470212
0.8828	High Similarity	NPC343720
0.8828	High Similarity	NPC473853
0.8828	High Similarity	NPC262156
0.8828	High Similarity	NPC184651
0.8828	High Similarity	NPC127389
0.8824	High Similarity	NPC209985
0.8824	High Similarity	NPC54743
0.8824	High Similarity	NPC472334
0.8824	High Similarity	NPC29799
0.8824	High Similarity	NPC306441
0.8824	High Similarity	NPC472336
0.8824	High Similarity	NPC156502
0.8824	High Similarity	NPC177160
0.8824	High Similarity	NPC471719
0.8824	High Similarity	NPC16435
0.8824	High Similarity	NPC10737
0.8824	High Similarity	NPC263367
0.8824	High Similarity	NPC477939
0.8819	High Similarity	NPC35071
0.8819	High Similarity	NPC177475
0.8819	High Similarity	NPC148615
0.8815	High Similarity	NPC67247
0.8815	High Similarity	NPC111635
0.8815	High Similarity	NPC478085
0.8806	High Similarity	NPC201587
0.8806	High Similarity	NPC253105
0.8803	High Similarity	NPC476348
0.8803	High Similarity	NPC187398
0.8803	High Similarity	NPC472969
0.8797	High Similarity	NPC469614
0.8797	High Similarity	NPC469612
0.8794	High Similarity	NPC199928
0.8788	High Similarity	NPC98631
0.8788	High Similarity	NPC128208
0.8788	High Similarity	NPC470084
0.8788	High Similarity	NPC129570
0.8788	High Similarity	NPC282703
0.8788	High Similarity	NPC470213
0.8788	High Similarity	NPC45774
0.8788	High Similarity	NPC184733
0.8788	High Similarity	NPC206615
0.8788	High Similarity	NPC11258
0.8788	High Similarity	NPC186843
0.8788	High Similarity	NPC21867
0.8786	High Similarity	NPC232228
0.8777	High Similarity	NPC67467
0.8769	High Similarity	NPC246704
0.876	High Similarity	NPC209567
0.8759	High Similarity	NPC470413
0.8759	High Similarity	NPC138738
0.8759	High Similarity	NPC470769
0.875	High Similarity	NPC112246
0.875	High Similarity	NPC61946
0.875	High Similarity	NPC207613
0.875	High Similarity	NPC121812
0.875	High Similarity	NPC234333
0.875	High Similarity	NPC112939
0.875	High Similarity	NPC189844
0.875	High Similarity	NPC109083
0.875	High Similarity	NPC224814
0.875	High Similarity	NPC14007
0.875	High Similarity	NPC260898
0.875	High Similarity	NPC269843
0.875	High Similarity	NPC470356
0.875	High Similarity	NPC474206
0.875	High Similarity	NPC47398
0.875	High Similarity	NPC60962
0.875	High Similarity	NPC94750
0.8741	High Similarity	NPC475250
0.8741	High Similarity	NPC106138
0.8741	High Similarity	NPC98809
0.8741	High Similarity	NPC476394
0.8741	High Similarity	NPC229442
0.8741	High Similarity	NPC168059
0.874	High Similarity	NPC135961
0.874	High Similarity	NPC181969
0.874	High Similarity	NPC320987
0.8731	High Similarity	NPC474017
0.8731	High Similarity	NPC27843
0.8731	High Similarity	NPC115207
0.8731	High Similarity	NPC228346
0.8731	High Similarity	NPC161557

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 NPC249791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	867
0.2-0.3	1776
0.3-0.4	2702
0.4-0.5	1723
0.5-0.6	947
0.6-0.7	692
0.7-0.8	154
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD3027	Phase 3
0.855	High Similarity	NPD4379	Clinical (unspecified phase)
0.8529	High Similarity	NPD1613	Approved
0.8529	High Similarity	NPD1612	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7266	Discontinued
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1934	Approved
0.811	Intermediate Similarity	NPD228	Approved
0.8108	Intermediate Similarity	NPD1653	Approved
0.8015	Intermediate Similarity	NPD5536	Phase 2
0.7974	Intermediate Similarity	NPD3882	Suspended
0.7961	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2801	Approved
0.7899	Intermediate Similarity	NPD9494	Approved
0.7877	Intermediate Similarity	NPD4628	Phase 3
0.7872	Intermediate Similarity	NPD1558	Phase 1
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6166	Phase 2
0.7848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD5283	Phase 1
0.7823	Intermediate Similarity	NPD6190	Approved
0.777	Intermediate Similarity	NPD2861	Phase 2
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7746	Intermediate Similarity	NPD4060	Phase 1
0.7734	Intermediate Similarity	NPD2684	Approved
0.7718	Intermediate Similarity	NPD1511	Approved
0.7702	Intermediate Similarity	NPD7054	Approved
0.7654	Intermediate Similarity	NPD7472	Approved
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7634	Intermediate Similarity	NPD7843	Approved
0.7622	Intermediate Similarity	NPD3620	Phase 2
0.7622	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1512	Approved
0.7609	Intermediate Similarity	NPD2983	Phase 2
0.7609	Intermediate Similarity	NPD2982	Phase 2
0.76	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7157	Approved
0.7591	Intermediate Similarity	NPD3705	Approved
0.7591	Intermediate Similarity	NPD1091	Approved
0.7589	Intermediate Similarity	NPD4908	Phase 1
0.7586	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4536	Approved
0.7586	Intermediate Similarity	NPD4538	Approved
0.7569	Intermediate Similarity	NPD4340	Discontinued
0.7568	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3060	Approved
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7556	Intermediate Similarity	NPD1548	Phase 1
0.7552	Intermediate Similarity	NPD6233	Phase 2
0.7538	Intermediate Similarity	NPD3021	Approved
0.7538	Intermediate Similarity	NPD3022	Approved
0.7536	Intermediate Similarity	NPD2981	Phase 2
0.7519	Intermediate Similarity	NPD290	Approved
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7518	Intermediate Similarity	NPD3018	Phase 2
0.7516	Intermediate Similarity	NPD3686	Approved
0.7516	Intermediate Similarity	NPD3687	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD4357	Discontinued
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD422	Phase 1
0.7464	Intermediate Similarity	NPD1610	Phase 2
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.745	Intermediate Similarity	NPD6674	Discontinued
0.745	Intermediate Similarity	NPD4237	Approved
0.745	Intermediate Similarity	NPD4162	Approved
0.745	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD4236	Phase 3
0.7448	Intermediate Similarity	NPD230	Phase 1
0.7442	Intermediate Similarity	NPD968	Approved
0.7434	Intermediate Similarity	NPD4123	Phase 3
0.7421	Intermediate Similarity	NPD6234	Discontinued
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.7415	Intermediate Similarity	NPD5960	Phase 3
0.7415	Intermediate Similarity	NPD5588	Approved
0.7413	Intermediate Similarity	NPD7095	Approved
0.741	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7808	Phase 3
0.7402	Intermediate Similarity	NPD291	Approved
0.74	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4110	Phase 3
0.7397	Intermediate Similarity	NPD6653	Approved
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1358	Approved
0.7383	Intermediate Similarity	NPD2424	Discontinued
0.7361	Intermediate Similarity	NPD6798	Discontinued
0.7361	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2677	Approved
0.7349	Intermediate Similarity	NPD7685	Pre-registration
0.7349	Intermediate Similarity	NPD6559	Discontinued
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6671	Approved
0.7329	Intermediate Similarity	NPD8127	Discontinued
0.7329	Intermediate Similarity	NPD6355	Discontinued
0.7329	Intermediate Similarity	NPD447	Suspended
0.7325	Intermediate Similarity	NPD37	Approved
0.7324	Intermediate Similarity	NPD6584	Phase 3
0.7319	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD6516	Phase 2
0.7315	Intermediate Similarity	NPD5763	Approved
0.7315	Intermediate Similarity	NPD5762	Approved
0.731	Intermediate Similarity	NPD4062	Phase 3
0.7308	Intermediate Similarity	NPD4678	Approved
0.7308	Intermediate Similarity	NPD4675	Approved
0.7305	Intermediate Similarity	NPD8651	Approved
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7296	Intermediate Similarity	NPD4965	Approved
0.7296	Intermediate Similarity	NPD4966	Approved
0.7296	Intermediate Similarity	NPD4967	Phase 2
0.7286	Intermediate Similarity	NPD2235	Phase 2
0.7286	Intermediate Similarity	NPD2231	Phase 2
0.7278	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD2977	Approved
0.7278	Intermediate Similarity	NPD2978	Approved
0.7273	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD1549	Phase 2
0.7255	Intermediate Similarity	NPD6799	Approved
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7248	Intermediate Similarity	NPD2935	Discontinued
0.7248	Intermediate Similarity	NPD1551	Phase 2
0.7246	Intermediate Similarity	NPD7039	Approved
0.7246	Intermediate Similarity	NPD7038	Approved
0.7239	Intermediate Similarity	NPD5535	Approved
0.7233	Intermediate Similarity	NPD5402	Approved
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7228	Approved
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5735	Approved
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3536	Discontinued
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1375	Discontinued
0.7192	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7185	Intermediate Similarity	NPD1241	Discontinued
0.7181	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3134	Approved
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.7171	Intermediate Similarity	NPD6331	Phase 2
0.717	Intermediate Similarity	NPD5773	Approved
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5772	Approved
0.7163	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6386	Approved
0.7152	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD1774	Approved
0.7143	Intermediate Similarity	NPD4140	Approved
0.7134	Intermediate Similarity	NPD3455	Phase 2
0.7134	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6032	Approved
0.7133	Intermediate Similarity	NPD2796	Approved
0.7125	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5585	Approved
0.7115	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5403	Approved
0.7113	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4749	Approved
0.7113	Intermediate Similarity	NPD6582	Phase 2
0.7113	Intermediate Similarity	NPD6583	Phase 3
0.7107	Intermediate Similarity	NPD6801	Discontinued
0.7105	Intermediate Similarity	NPD5177	Phase 3
0.7101	Intermediate Similarity	NPD7549	Discontinued
0.7092	Intermediate Similarity	NPD1535	Discovery
0.7073	Intermediate Similarity	NPD6232	Discontinued
0.7071	Intermediate Similarity	NPD4626	Approved
0.7071	Intermediate Similarity	NPD1778	Approved
0.7067	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD3225	Approved
0.7059	Intermediate Similarity	NPD4535	Phase 3
0.7059	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD3179	Approved
0.7055	Intermediate Similarity	NPD3180	Approved
0.7051	Intermediate Similarity	NPD52	Approved
0.7051	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7526	Approved
0.705	Intermediate Similarity	NPD1894	Discontinued
0.7047	Intermediate Similarity	NPD3052	Approved
0.7047	Intermediate Similarity	NPD3054	Approved
0.7042	Intermediate Similarity	NPD1481	Phase 2
0.703	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1240	Approved
0.7027	Intermediate Similarity	NPD3061	Approved
0.7027	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3062	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data