NPASS Compound

Structure

CID324386 OpenBabel06191716172D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 -0.0000 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 3.4641 -3.0000 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 4.3301 -3.5000 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 2.5981 -0.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 1.7321 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 3 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 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 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 1.7321 1.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.995
LogD:	2.461
LogS:	-3.597
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	2.946
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.856
MDCK Permeability:	7.996004569577053e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.17
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	97.12642669677734%
Volume Distribution (VD):	0.406
Pgp-substrate:	2.2991864681243896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.758
CYP1A2-substrate:	0.593
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.855
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.63
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	15.753
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.208
Skin Sensitization:	0.927
Carcinogencity:	0.518
Eye Corrosion:	0.004
Eye Irritation:	0.933
Respiratory Toxicity:	0.308

Download Data

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

Natural Product: NPC324386

Natural Product ID:	NPC324386
*Common Name:**	5,7-Dihydroxy-2-(4-Hydroxyphenyl)-6-Methyl-2,3-Dihydrochromen-4-One
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methyl-2,3-dihydrochromen-4-one
Synonyms:	NSC-180246
Standard InCHIKey:	SLFZBNOERHGNMI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-8-11(18)6-14-15(16(8)20)12(19)7-13(21-14)9-2-4-10(17)5-3-9/h2-6,13,17-18,20H,7H2,1H3
SMILES:	Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(c(c2O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484640
PubChem CID:	301798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	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
ED50	1
IC50	8
Potency	24

Activity Type	# Activity
Cell Line	1
Individual Protein	23
Organism	2
Others	3
PROTEIN COMPLEX	3
Protein-Protein Interaction	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	57.0	ug ml-1	PMID[523589]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	25118.9	nM	PMID[523590]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	=	4466.8	nM	PMID[523590]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	17782.8	nM	PMID[523590]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	3944.08	nM	PMID[523590]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	1258.9	nM	PMID[523590]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[523590]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[523590]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[523590]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[523590]
NPT3938	Individual Protein	Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1	Homo sapiens	IC50	=	4744.0	nM	PMID[523590]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[523590]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	n.a.	5011.9	nM	PMID[523590]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[523590]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	125892.5	nM	PMID[523590]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	1584.9	nM	PMID[523590]
NPT1040	Individual Protein	Human immunodeficiency virus type 1 Tat protein	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)	IC50	n.a.	37150.0	nM	PMID[523590]
NPT3937	Protein-Protein Interaction	Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1	Homo sapiens	IC50	=	13100.0	nM	PMID[523590]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PMID[523590]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	3981.1	nM	PMID[523590]
NPT3937	Protein-Protein Interaction	Voltage-gated N-type calcium channel alpha-1B subunit/Amyloid beta A4 precursor protein-binding family A member 1	Homo sapiens	IC50	>	50000.0	nM	PMID[523590]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5858.4	nM	PMID[523590]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	5804.8	nM	PMID[523590]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[523590]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[523590]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[523590]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	n.a.	6701.6	nM	PMID[523590]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[523590]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[523590]
NPT2	Others	Unspecified		IC50	=	13273.0	nM	PMID[523590]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	95283.4	nM	PMID[523590]
NPT2	Others	Unspecified		IC50	=	9391.0	nM	PMID[523590]
NPT2	Others	Unspecified		IC50	n.a.	2680.0	nM	PMID[523590]

☑ 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 NPC324386 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	354
0.1-0.2	1539
0.2-0.3	3908
0.3-0.4	10372
0.4-0.5	7960
0.5-0.6	3567
0.6-0.7	5625
0.7-0.8	5173
0.8-0.85	2123
0.85-0.9	1215
0.9-0.95	620
0.95-1	241

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC312391
1.0	High Similarity	NPC213322
1.0	High Similarity	NPC4743
0.9926	High Similarity	NPC64915
0.9926	High Similarity	NPC223500
0.9926	High Similarity	NPC220998
0.9926	High Similarity	NPC32739
0.9926	High Similarity	NPC66515
0.9926	High Similarity	NPC166934
0.9926	High Similarity	NPC194432
0.9926	High Similarity	NPC328164
0.9926	High Similarity	NPC148757
0.9926	High Similarity	NPC40833
0.9926	High Similarity	NPC166482
0.9926	High Similarity	NPC177354
0.9926	High Similarity	NPC76338
0.9926	High Similarity	NPC296917
0.9926	High Similarity	NPC324436
0.9926	High Similarity	NPC10937
0.9926	High Similarity	NPC227579
0.9926	High Similarity	NPC265040
0.9926	High Similarity	NPC306829
0.9926	High Similarity	NPC76372
0.9926	High Similarity	NPC125855
0.9926	High Similarity	NPC37496
0.9926	High Similarity	NPC182852
0.9926	High Similarity	NPC161506
0.9926	High Similarity	NPC228504
0.9926	High Similarity	NPC167624
0.9926	High Similarity	NPC107572
0.9926	High Similarity	NPC324134
0.9926	High Similarity	NPC78
0.9926	High Similarity	NPC1089
0.9854	High Similarity	NPC85162
0.9854	High Similarity	NPC150408
0.9854	High Similarity	NPC164980
0.9854	High Similarity	NPC223812
0.9854	High Similarity	NPC316816
0.9854	High Similarity	NPC39329
0.9854	High Similarity	NPC214166
0.9854	High Similarity	NPC310130
0.9854	High Similarity	NPC91560
0.9854	High Similarity	NPC75049
0.9854	High Similarity	NPC143896
0.9854	High Similarity	NPC185276
0.9854	High Similarity	NPC125894
0.9854	High Similarity	NPC175504
0.9854	High Similarity	NPC478086
0.9854	High Similarity	NPC149026
0.9854	High Similarity	NPC77794
0.9854	High Similarity	NPC68104
0.9854	High Similarity	NPC169591
0.9854	High Similarity	NPC107177
0.9854	High Similarity	NPC81697
0.9854	High Similarity	NPC257097
0.9854	High Similarity	NPC278249
0.9854	High Similarity	NPC221432
0.9853	High Similarity	NPC110038
0.9853	High Similarity	NPC3188
0.9853	High Similarity	NPC166689
0.9853	High Similarity	NPC258630
0.9853	High Similarity	NPC279650
0.9853	High Similarity	NPC17170
0.9853	High Similarity	NPC96408
0.9853	High Similarity	NPC248372
0.9853	High Similarity	NPC156190
0.9852	High Similarity	NPC274784
0.9852	High Similarity	NPC150648
0.9852	High Similarity	NPC329203
0.9852	High Similarity	NPC222342
0.9852	High Similarity	NPC225153
0.9852	High Similarity	NPC265871
0.9852	High Similarity	NPC310135
0.9852	High Similarity	NPC20709
0.9783	High Similarity	NPC209040
0.9783	High Similarity	NPC235217
0.9783	High Similarity	NPC473013
0.9783	High Similarity	NPC473014
0.9783	High Similarity	NPC236766
0.9783	High Similarity	NPC473015
0.9783	High Similarity	NPC131568
0.9783	High Similarity	NPC197252
0.9783	High Similarity	NPC131579
0.9779	High Similarity	NPC6407
0.9779	High Similarity	NPC110228
0.9779	High Similarity	NPC188243
0.9712	High Similarity	NPC267375
0.9712	High Similarity	NPC54577
0.9712	High Similarity	NPC214774
0.9712	High Similarity	NPC470132
0.9712	High Similarity	NPC470131
0.9712	High Similarity	NPC301276
0.9712	High Similarity	NPC470134
0.9712	High Similarity	NPC176229
0.9712	High Similarity	NPC142405
0.9712	High Similarity	NPC109183
0.9712	High Similarity	NPC312973
0.9712	High Similarity	NPC195621
0.9712	High Similarity	NPC20488
0.9712	High Similarity	NPC475052
0.9712	High Similarity	NPC472629
0.9712	High Similarity	NPC83357
0.9712	High Similarity	NPC127059
0.9712	High Similarity	NPC285630
0.9712	High Similarity	NPC67805
0.9712	High Similarity	NPC470133
0.9712	High Similarity	NPC246948
0.9712	High Similarity	NPC111786
0.9712	High Similarity	NPC88964
0.9712	High Similarity	NPC470647
0.9712	High Similarity	NPC473078
0.9706	High Similarity	NPC78913
0.9706	High Similarity	NPC18260
0.9706	High Similarity	NPC140890
0.9704	High Similarity	NPC13768
0.9704	High Similarity	NPC243083
0.9704	High Similarity	NPC32441
0.9704	High Similarity	NPC295261
0.9704	High Similarity	NPC296490
0.9704	High Similarity	NPC107586
0.9704	High Similarity	NPC287246
0.9704	High Similarity	NPC12296
0.9704	High Similarity	NPC79943
0.9643	High Similarity	NPC473077
0.9643	High Similarity	NPC283234
0.9643	High Similarity	NPC300988
0.9643	High Similarity	NPC472627
0.9643	High Similarity	NPC110303
0.9643	High Similarity	NPC23728
0.9643	High Similarity	NPC296998
0.9643	High Similarity	NPC10990
0.964	High Similarity	NPC319752
0.964	High Similarity	NPC470136
0.964	High Similarity	NPC124780
0.964	High Similarity	NPC110776
0.964	High Similarity	NPC470135
0.964	High Similarity	NPC271288
0.964	High Similarity	NPC271590
0.964	High Similarity	NPC39045
0.964	High Similarity	NPC470890
0.964	High Similarity	NPC87486
0.9638	High Similarity	NPC147145
0.9635	High Similarity	NPC76445
0.9635	High Similarity	NPC284550
0.9635	High Similarity	NPC241100
0.9635	High Similarity	NPC69769
0.9635	High Similarity	NPC159275
0.9635	High Similarity	NPC129853
0.9632	High Similarity	NPC118813
0.9632	High Similarity	NPC201395
0.9632	High Similarity	NPC472460
0.9632	High Similarity	NPC99333
0.9632	High Similarity	NPC147686
0.9632	High Similarity	NPC188947
0.9632	High Similarity	NPC329225
0.9632	High Similarity	NPC280284
0.9574	High Similarity	NPC161191
0.9574	High Similarity	NPC132592
0.9574	High Similarity	NPC160821
0.9571	High Similarity	NPC2416
0.9571	High Similarity	NPC290133
0.9571	High Similarity	NPC474161
0.9571	High Similarity	NPC476153
0.9571	High Similarity	NPC228779
0.9571	High Similarity	NPC187282
0.9571	High Similarity	NPC24136
0.9571	High Similarity	NPC215885
0.9571	High Similarity	NPC476088
0.9568	High Similarity	NPC166138
0.9568	High Similarity	NPC18585
0.9568	High Similarity	NPC106985
0.9568	High Similarity	NPC471621
0.9565	High Similarity	NPC110969
0.9565	High Similarity	NPC282300
0.9562	High Similarity	NPC216978
0.9562	High Similarity	NPC55018
0.9562	High Similarity	NPC301217
0.9562	High Similarity	NPC220062
0.9562	High Similarity	NPC303633
0.9562	High Similarity	NPC217186
0.9562	High Similarity	NPC53181
0.9562	High Similarity	NPC96565
0.9562	High Similarity	NPC261234
0.9559	High Similarity	NPC476480
0.9559	High Similarity	NPC259685
0.9559	High Similarity	NPC290291
0.9559	High Similarity	NPC275055
0.9559	High Similarity	NPC84585
0.9507	High Similarity	NPC473016
0.9507	High Similarity	NPC3642
0.9507	High Similarity	NPC472628
0.9504	High Similarity	NPC308200
0.95	High Similarity	NPC224714
0.9496	High Similarity	NPC144499
0.9496	High Similarity	NPC202981
0.9496	High Similarity	NPC73028
0.9496	High Similarity	NPC11561
0.9496	High Similarity	NPC226636
0.9496	High Similarity	NPC266725
0.9493	High Similarity	NPC270883

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 NPC324386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	944
0.2-0.3	1508
0.3-0.4	2582
0.4-0.5	1889
0.5-0.6	1197
0.6-0.7	494
0.7-0.8	146
0.8-0.85	45
0.85-0.9	17
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9704	High Similarity	NPD1550	Clinical (unspecified phase)
0.9704	High Similarity	NPD1552	Clinical (unspecified phase)
0.9632	High Similarity	NPD1549	Phase 2
0.9362	High Similarity	NPD4378	Clinical (unspecified phase)
0.9247	High Similarity	NPD2393	Clinical (unspecified phase)
0.9184	High Similarity	NPD8443	Clinical (unspecified phase)
0.913	High Similarity	NPD1510	Phase 2
0.9118	High Similarity	NPD1240	Approved
0.911	High Similarity	NPD7411	Suspended
0.9091	High Similarity	NPD7410	Clinical (unspecified phase)
0.9065	High Similarity	NPD2796	Approved
0.906	High Similarity	NPD7075	Discontinued
0.9048	High Similarity	NPD1934	Approved
0.9041	High Similarity	NPD4380	Phase 2
0.8986	High Similarity	NPD7096	Clinical (unspecified phase)
0.8986	High Similarity	NPD1607	Approved
0.8859	High Similarity	NPD7819	Suspended
0.8792	High Similarity	NPD6801	Discontinued
0.8684	High Similarity	NPD4381	Clinical (unspecified phase)
0.8636	High Similarity	NPD6959	Discontinued
0.863	High Similarity	NPD6799	Approved
0.863	High Similarity	NPD1511	Approved
0.8611	High Similarity	NPD7421	Clinical (unspecified phase)
0.859	High Similarity	NPD7852	Clinical (unspecified phase)
0.8544	High Similarity	NPD7804	Clinical (unspecified phase)
0.8514	High Similarity	NPD1512	Approved
0.8497	Intermediate Similarity	NPD7768	Phase 2
0.8487	Intermediate Similarity	NPD2801	Approved
0.8483	Intermediate Similarity	NPD2800	Approved
0.8471	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8429	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD3750	Approved
0.8411	Intermediate Similarity	NPD6599	Discontinued
0.8403	Intermediate Similarity	NPD1551	Phase 2
0.8377	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD3749	Approved
0.8322	Intermediate Similarity	NPD6651	Approved
0.8309	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7074	Phase 3
0.8231	Intermediate Similarity	NPD1243	Approved
0.8212	Intermediate Similarity	NPD920	Approved
0.8212	Intermediate Similarity	NPD5403	Approved
0.82	Intermediate Similarity	NPD5401	Approved
0.8199	Intermediate Similarity	NPD7054	Approved
0.8194	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6559	Discontinued
0.8151	Intermediate Similarity	NPD2935	Discontinued
0.8148	Intermediate Similarity	NPD7472	Approved
0.8141	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5953	Discontinued
0.8098	Intermediate Similarity	NPD6797	Phase 2
0.8095	Intermediate Similarity	NPD2344	Approved
0.8086	Intermediate Similarity	NPD7286	Phase 2
0.8082	Intermediate Similarity	NPD2799	Discontinued
0.8082	Intermediate Similarity	NPD3748	Approved
0.8079	Intermediate Similarity	NPD2534	Approved
0.8079	Intermediate Similarity	NPD2533	Approved
0.8079	Intermediate Similarity	NPD2532	Approved
0.8079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1203	Approved
0.8054	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7251	Discontinued
0.8043	Intermediate Similarity	NPD1610	Phase 2
0.8042	Intermediate Similarity	NPD2313	Discontinued
0.8028	Intermediate Similarity	NPD4908	Phase 1
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7975	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7959	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7033	Discontinued
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7905	Intermediate Similarity	NPD6099	Approved
0.7905	Intermediate Similarity	NPD6100	Approved
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7892	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2309	Approved
0.7877	Intermediate Similarity	NPD5124	Phase 1
0.7877	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3226	Approved
0.7857	Intermediate Similarity	NPD9717	Approved
0.7852	Intermediate Similarity	NPD2346	Discontinued
0.7849	Intermediate Similarity	NPD4363	Phase 3
0.7849	Intermediate Similarity	NPD4360	Phase 2
0.7848	Intermediate Similarity	NPD5402	Approved
0.7812	Intermediate Similarity	NPD919	Approved
0.7808	Intermediate Similarity	NPD943	Approved
0.7793	Intermediate Similarity	NPD3268	Approved
0.7786	Intermediate Similarity	NPD422	Phase 1
0.7716	Intermediate Similarity	NPD1247	Approved
0.7697	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2797	Approved
0.7687	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1613	Approved
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7390	Discontinued
0.7657	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD2798	Approved
0.7635	Intermediate Similarity	NPD1933	Approved
0.7632	Intermediate Similarity	NPD2654	Approved
0.7626	Intermediate Similarity	NPD9545	Approved
0.7622	Intermediate Similarity	NPD3225	Approved
0.7613	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD1729	Discontinued
0.7603	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD4308	Phase 3
0.76	Intermediate Similarity	NPD4361	Phase 2
0.76	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3266	Approved
0.7569	Intermediate Similarity	NPD3267	Approved
0.7562	Intermediate Similarity	NPD1465	Phase 2
0.7561	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD5710	Approved
0.7551	Intermediate Similarity	NPD6798	Discontinued
0.7534	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1241	Discontinued
0.7517	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3926	Phase 2
0.7483	Intermediate Similarity	NPD1608	Approved
0.7483	Intermediate Similarity	NPD3972	Approved
0.7482	Intermediate Similarity	NPD9493	Approved
0.7466	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5889	Approved
0.7438	Intermediate Similarity	NPD5890	Approved
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.743	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7458	Discontinued
0.7413	Intermediate Similarity	NPD1201	Approved
0.7412	Intermediate Similarity	NPD6104	Discontinued
0.7407	Intermediate Similarity	NPD4288	Approved
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD230	Phase 1
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7386	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3751	Discontinued
0.7377	Intermediate Similarity	NPD7584	Approved
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7347	Intermediate Similarity	NPD2861	Phase 2
0.7338	Intermediate Similarity	NPD2424	Discontinued
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7329	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD1470	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7325	Intermediate Similarity	NPD7212	Phase 2
0.7325	Intermediate Similarity	NPD7213	Phase 3
0.7315	Intermediate Similarity	NPD3764	Approved
0.7315	Intermediate Similarity	NPD411	Approved
0.7315	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD4749	Approved
0.7301	Intermediate Similarity	NPD2296	Approved
0.729	Intermediate Similarity	NPD1652	Phase 2
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD447	Suspended
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7278	Intermediate Similarity	NPD4662	Approved
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD6585	Discontinued
0.7262	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1894	Discontinued
0.7248	Intermediate Similarity	NPD3027	Phase 3
0.7246	Intermediate Similarity	NPD3787	Discontinued
0.7244	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7239	Intermediate Similarity	NPD8455	Phase 2
0.7219	Intermediate Similarity	NPD3142	Approved
0.7219	Intermediate Similarity	NPD3140	Approved
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5406	Approved
0.7208	Intermediate Similarity	NPD5404	Approved
0.7208	Intermediate Similarity	NPD5408	Approved
0.7208	Intermediate Similarity	NPD4476	Approved
0.7208	Intermediate Similarity	NPD5405	Approved
0.7208	Intermediate Similarity	NPD4477	Approved
0.7197	Intermediate Similarity	NPD3887	Approved
0.7197	Intermediate Similarity	NPD2354	Approved
0.7186	Intermediate Similarity	NPD7199	Phase 2
0.7178	Intermediate Similarity	NPD7577	Discontinued
0.7172	Intermediate Similarity	NPD1535	Discovery
0.717	Intermediate Similarity	NPD7447	Phase 1
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD6002	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