NPASS Compound

Structure

NPC474638 OpenBabel07101719522D 23 25 0 0 1 0 0 0 0 0999 V2000 0.5176 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7765 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7424 3.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 2.4495 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 1.0000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0012 4.1225 0.0000 O 0 0 0 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 3.4154 2.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 7 23 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	302.699
LogP:	1.384
LogD:	0.683
LogS:	-2.84
# Rotatable Bonds:	2
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	3.44
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.484
MDCK Permeability:	8.785733371041715e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.293
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	95.94719696044922%
Volume Distribution (VD):	0.456
Pgp-substrate:	3.9048404693603516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.636
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.146
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.602
CYP2C9-substrate:	0.64
CYP2D6-inhibitor:	0.213
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.396
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	13.393
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.6
AMES Toxicity:	0.804
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.945
Carcinogencity:	0.221
Eye Corrosion:	0.003
Eye Irritation:	0.903
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: NPC474638

Natural Product ID:	NPC474638
*Common Name:**	Hematoxylone
IUPAC Name:	(3R)-3-[(3,4-dihydroxyphenyl)methyl]-3,7,8-trihydroxy-2H-chromen-4-one
Synonyms:	Hematoxylone
Standard InCHIKey:	JUJOJJFIOBKCID-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C16H14O7/c17-10-3-1-8(5-12(10)19)6-16(22)7-23-14-9(15(16)21)2-4-11(18)13(14)20/h1-5,17-20,22H,6-7H2/t16-/m1/s1
SMILES:	C1C(C(=O)C2=C(O1)C(=C(C=C2)O)O)(CC3=CC(=C(C=C3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477768
PubChem CID:	44578561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]

☑ 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	5
Others	7

Activity Type	# Activity
Individual Protein	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	94.8	%	PMID[529052]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	84.8	%	PMID[529052]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	89.6	%	PMID[529052]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	86.2	%	PMID[529052]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	96.7	%	PMID[529052]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	91.5	%	PMID[529052]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	93.0	%	PMID[529052]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	1800.0	nM	PMID[529052]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	850.0	nM	PMID[529052]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	IC50	=	2900.0	nM	PMID[529052]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	6100.0	nM	PMID[529052]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	IC50	=	3200.0	nM	PMID[529052]

☑ 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 NPC474638 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	436
0.1-0.2	1827
0.2-0.3	4784
0.3-0.4	10588
0.4-0.5	6794
0.5-0.6	3520
0.6-0.7	4879
0.7-0.8	5257
0.8-0.85	2525
0.85-0.9	1399
0.9-0.95	642
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC55738
0.9865	High Similarity	NPC141212
0.98	High Similarity	NPC67876
0.9669	High Similarity	NPC52530
0.9608	High Similarity	NPC173137
0.9608	High Similarity	NPC308992
0.9605	High Similarity	NPC152904
0.9603	High Similarity	NPC320825
0.9603	High Similarity	NPC13858
0.9603	High Similarity	NPC326037
0.96	High Similarity	NPC27532
0.96	High Similarity	NPC256346
0.96	High Similarity	NPC325028
0.96	High Similarity	NPC246328
0.9597	High Similarity	NPC31363
0.9542	High Similarity	NPC263449
0.9539	High Similarity	NPC299520
0.9539	High Similarity	NPC99597
0.9539	High Similarity	NPC129684
0.9539	High Similarity	NPC471479
0.9539	High Similarity	NPC210084
0.9539	High Similarity	NPC471515
0.9536	High Similarity	NPC2928
0.9533	High Similarity	NPC240476
0.9533	High Similarity	NPC477231
0.9533	High Similarity	NPC9743
0.9533	High Similarity	NPC55205
0.9533	High Similarity	NPC61506
0.9533	High Similarity	NPC260491
0.9533	High Similarity	NPC302950
0.9533	High Similarity	NPC257648
0.9533	High Similarity	NPC219582
0.9533	High Similarity	NPC36835
0.9533	High Similarity	NPC236637
0.9533	High Similarity	NPC246162
0.953	High Similarity	NPC29231
0.9527	High Similarity	NPC43669
0.9527	High Similarity	NPC196277
0.9527	High Similarity	NPC272721
0.9474	High Similarity	NPC250922
0.9474	High Similarity	NPC303255
0.9474	High Similarity	NPC201837
0.9474	High Similarity	NPC471500
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC472916
0.9474	High Similarity	NPC255106
0.9474	High Similarity	NPC265511
0.947	High Similarity	NPC18727
0.947	High Similarity	NPC167091
0.947	High Similarity	NPC88645
0.947	High Similarity	NPC292214
0.947	High Similarity	NPC469550
0.947	High Similarity	NPC206238
0.947	High Similarity	NPC271779
0.9467	High Similarity	NPC125062
0.9467	High Similarity	NPC54394
0.9467	High Similarity	NPC252933
0.9467	High Similarity	NPC200740
0.9467	High Similarity	NPC251110
0.9463	High Similarity	NPC105512
0.9463	High Similarity	NPC183959
0.9463	High Similarity	NPC1612
0.9459	High Similarity	NPC77378
0.9459	High Similarity	NPC95864
0.9423	High Similarity	NPC224280
0.9423	High Similarity	NPC234052
0.9423	High Similarity	NPC62261
0.9416	High Similarity	NPC282009
0.9416	High Similarity	NPC287328
0.9416	High Similarity	NPC470183
0.9412	High Similarity	NPC474836
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC48208
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC156057
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC162869
0.9412	High Similarity	NPC472911
0.9412	High Similarity	NPC245758
0.9412	High Similarity	NPC27337
0.9412	High Similarity	NPC474208
0.9412	High Similarity	NPC475267
0.9408	High Similarity	NPC201451
0.9408	High Similarity	NPC255807
0.9408	High Similarity	NPC168247
0.9408	High Similarity	NPC256925
0.9408	High Similarity	NPC57674
0.9408	High Similarity	NPC31018
0.9408	High Similarity	NPC152951
0.9408	High Similarity	NPC44079
0.9408	High Similarity	NPC117992
0.9408	High Similarity	NPC26227
0.9408	High Similarity	NPC230149
0.9404	High Similarity	NPC39007
0.9404	High Similarity	NPC60972
0.9404	High Similarity	NPC199100
0.9404	High Similarity	NPC19721
0.9404	High Similarity	NPC39732
0.9404	High Similarity	NPC180234
0.9404	High Similarity	NPC101996
0.9404	High Similarity	NPC120537
0.9404	High Similarity	NPC472912
0.9404	High Similarity	NPC279989
0.9404	High Similarity	NPC260979
0.9404	High Similarity	NPC161277
0.9404	High Similarity	NPC82325
0.94	High Similarity	NPC248102
0.94	High Similarity	NPC61620
0.94	High Similarity	NPC267117
0.9396	High Similarity	NPC294852
0.9396	High Similarity	NPC3036
0.9396	High Similarity	NPC321011
0.9396	High Similarity	NPC188679
0.9392	High Similarity	NPC229190
0.9363	High Similarity	NPC477517
0.9359	High Similarity	NPC124038
0.9359	High Similarity	NPC41301
0.9359	High Similarity	NPC472625
0.9355	High Similarity	NPC471499
0.9355	High Similarity	NPC134783
0.9351	High Similarity	NPC204879
0.9351	High Similarity	NPC22192
0.9346	High Similarity	NPC43243
0.9346	High Similarity	NPC35038
0.9346	High Similarity	NPC266960
0.9346	High Similarity	NPC472455
0.9346	High Similarity	NPC98661
0.9346	High Similarity	NPC133970
0.9346	High Similarity	NPC245546
0.9346	High Similarity	NPC195796
0.9346	High Similarity	NPC278778
0.9346	High Similarity	NPC247017
0.9346	High Similarity	NPC6633
0.9346	High Similarity	NPC5322
0.9346	High Similarity	NPC291878
0.9346	High Similarity	NPC49824
0.9342	High Similarity	NPC273462
0.9342	High Similarity	NPC472915
0.9342	High Similarity	NPC78326
0.9342	High Similarity	NPC270620
0.9342	High Similarity	NPC33051
0.9342	High Similarity	NPC70433
0.9342	High Similarity	NPC227337
0.9342	High Similarity	NPC49402
0.9342	High Similarity	NPC236223
0.9342	High Similarity	NPC179126
0.9338	High Similarity	NPC171010
0.9338	High Similarity	NPC149614
0.9338	High Similarity	NPC471229
0.9338	High Similarity	NPC50403
0.9338	High Similarity	NPC225731
0.9338	High Similarity	NPC133953
0.9338	High Similarity	NPC28274
0.9338	High Similarity	NPC117579
0.9338	High Similarity	NPC204515
0.9338	High Similarity	NPC260895
0.9333	High Similarity	NPC137062
0.9333	High Similarity	NPC270465
0.9333	High Similarity	NPC159103
0.9333	High Similarity	NPC183950
0.9333	High Similarity	NPC195763
0.9333	High Similarity	NPC69430
0.9333	High Similarity	NPC264550
0.9333	High Similarity	NPC87125
0.9333	High Similarity	NPC264289
0.9333	High Similarity	NPC52005
0.9333	High Similarity	NPC333691
0.9333	High Similarity	NPC287101
0.9333	High Similarity	NPC142876
0.9333	High Similarity	NPC200060
0.9333	High Similarity	NPC223579
0.9333	High Similarity	NPC277032
0.9333	High Similarity	NPC139293
0.9333	High Similarity	NPC40290
0.9329	High Similarity	NPC74881
0.9329	High Similarity	NPC168803
0.9329	High Similarity	NPC51443
0.9329	High Similarity	NPC188074
0.9329	High Similarity	NPC125449
0.9299	High Similarity	NPC300053
0.9299	High Similarity	NPC108433
0.9295	High Similarity	NPC472964
0.9295	High Similarity	NPC474162
0.9295	High Similarity	NPC474034
0.9295	High Similarity	NPC472448
0.9295	High Similarity	NPC83922
0.9295	High Similarity	NPC474150
0.9295	High Similarity	NPC474033
0.929	High Similarity	NPC472902
0.929	High Similarity	NPC118256
0.929	High Similarity	NPC470326
0.929	High Similarity	NPC474960
0.929	High Similarity	NPC119209
0.929	High Similarity	NPC472624
0.929	High Similarity	NPC192686
0.929	High Similarity	NPC476980
0.929	High Similarity	NPC471744

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 NPC474638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	958
0.2-0.3	1860
0.3-0.4	2602
0.4-0.5	1718
0.5-0.6	972
0.6-0.7	435
0.7-0.8	136
0.8-0.85	31
0.85-0.9	11
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9533	High Similarity	NPD1934	Approved
0.9346	High Similarity	NPD3882	Suspended
0.9262	High Similarity	NPD1512	Approved
0.9216	High Similarity	NPD2393	Clinical (unspecified phase)
0.9216	High Similarity	NPD2801	Approved
0.9177	High Similarity	NPD6166	Phase 2
0.9177	High Similarity	NPD6168	Clinical (unspecified phase)
0.9177	High Similarity	NPD6167	Clinical (unspecified phase)
0.9128	High Similarity	NPD1511	Approved
0.8944	High Similarity	NPD3818	Discontinued
0.891	High Similarity	NPD3817	Phase 2
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8792	High Similarity	NPD1549	Phase 2
0.8788	High Similarity	NPD4338	Clinical (unspecified phase)
0.8725	High Similarity	NPD1552	Clinical (unspecified phase)
0.8725	High Similarity	NPD1550	Clinical (unspecified phase)
0.872	High Similarity	NPD7074	Phase 3
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8679	High Similarity	NPD7075	Discontinued
0.8667	High Similarity	NPD6797	Phase 2
0.8659	High Similarity	NPD7054	Approved
0.8654	High Similarity	NPD4380	Phase 2
0.8614	High Similarity	NPD7251	Discontinued
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8606	High Similarity	NPD7472	Approved
0.8591	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD5494	Approved
0.8563	High Similarity	NPD7808	Phase 3
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8554	High Similarity	NPD7993	Clinical (unspecified phase)
0.8506	High Similarity	NPD6799	Approved
0.8491	Intermediate Similarity	NPD1465	Phase 2
0.8446	Intermediate Similarity	NPD943	Approved
0.8323	Intermediate Similarity	NPD5402	Approved
0.8322	Intermediate Similarity	NPD1240	Approved
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8293	Intermediate Similarity	NPD1247	Approved
0.8289	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1607	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1613	Approved
0.82	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3926	Phase 2
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8113	Intermediate Similarity	NPD5403	Approved
0.811	Intermediate Similarity	NPD3749	Approved
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8105	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5401	Approved
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3751	Discontinued
0.8026	Intermediate Similarity	NPD230	Phase 1
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7962	Intermediate Similarity	NPD3750	Approved
0.7935	Intermediate Similarity	NPD1551	Phase 2
0.7911	Intermediate Similarity	NPD6190	Approved
0.7908	Intermediate Similarity	NPD447	Suspended
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7785	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7748	Intermediate Similarity	NPD9494	Approved
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD920	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3748	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD1653	Approved
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2313	Discontinued
0.7595	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2309	Approved
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7453	Intermediate Similarity	NPD1243	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7417	Intermediate Similarity	NPD9269	Phase 2
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD5242	Approved
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD37	Approved
0.733	Intermediate Similarity	NPD7228	Approved
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4965	Approved
0.7296	Intermediate Similarity	NPD6651	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7256	Intermediate Similarity	NPD2354	Approved
0.7251	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD5710	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7174	Intermediate Similarity	NPD4287	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7161	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD9268	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7112	Intermediate Similarity	NPD6535	Approved
0.711	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6233	Phase 2
0.71	Intermediate Similarity	NPD4665	Approved
0.71	Intermediate Similarity	NPD4111	Phase 1
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD1608	Approved
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7068	Intermediate Similarity	NPD3452	Approved
0.7068	Intermediate Similarity	NPD2493	Approved
0.7068	Intermediate Similarity	NPD2494	Approved
0.7068	Intermediate Similarity	NPD3450	Approved
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4288	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7044	Intermediate Similarity	NPD411	Approved
0.7044	Intermediate Similarity	NPD3268	Approved
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2163	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7032	Intermediate Similarity	NPD4749	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