NPASS Compound

Structure

NPC85624 OpenBabel07101718182D 30 32 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.3660 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 4.3301 1.5000 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 2.5981 -2.5000 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 -0.8660 1.5000 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 2.5981 -1.5000 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 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 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 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 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 8 1 1 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 29 1 1 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.15
Volume:	403.527
LogP:	-0.279
LogD:	-0.446
LogS:	-2.263
# Rotatable Bonds:	6
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	4.136
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.996
MDCK Permeability:	6.841393042122945e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.66
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	52.23517990112305%
Volume Distribution (VD):	0.423
Pgp-substrate:	27.805635452270508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	1.902
Half-life (T1/2):	0.482

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.547
Skin Sensitization:	0.092
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC85624

Natural Product ID:	NPC85624
*Common Name:**	Sid85149094
IUPAC Name:	6-[(2R)-2,3-dihydroxy-3-methylbutyl]-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Synonyms:
Standard InCHIKey:	DMCVVAVPFHUPNH-UPPPXSOGSA-N
Standard InCHI:	InChI=1S/C20H26O10/c1-20(2,27)14(22)6-10-5-9-3-4-15(23)28-11(9)7-12(10)29-19-18(26)17(25)16(24)13(8-21)30-19/h3-5,7,13-14,16-19,21-22,24-27H,6,8H2,1-2H3/t13-,14-,16-,17+,18-,19-/m1/s1
SMILES:	CC(C)([C@@H](Cc1cc2ccc(=O)oc2cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159420
PubChem CID:	44144279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0001743] Coumarin glycosides

*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
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	roots	Miyazaki prefecture, Japan	n.a.	PMID[9873511]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3509	Angelica furcijuga	Species	Apiaceae	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	2
Others	2
Potency	2

Activity Type	# Activity
Individual Protein	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	5.8	nM	PMID[550693]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	100000.0	nM	PMID[550692]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	5.8	%	PMID[550692]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[550692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	49.0	%	PMID[550692]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[550693]

☑ 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 NPC85624 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	370
0.1-0.2	1563
0.2-0.3	3516
0.3-0.4	8313
0.4-0.5	10211
0.5-0.6	4665
0.6-0.7	5693
0.7-0.8	5667
0.8-0.85	2005
0.85-0.9	601
0.9-0.95	88
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC296377
0.9856	High Similarity	NPC471764
0.9856	High Similarity	NPC87950
0.9786	High Similarity	NPC169510
0.9493	High Similarity	NPC312881
0.9489	High Similarity	NPC232246
0.9489	High Similarity	NPC153818
0.9424	High Similarity	NPC215512
0.9424	High Similarity	NPC195357
0.9424	High Similarity	NPC476442
0.9424	High Similarity	NPC152771
0.9424	High Similarity	NPC287286
0.942	High Similarity	NPC279573
0.9416	High Similarity	NPC103409
0.9416	High Similarity	NPC224543
0.9416	High Similarity	NPC188380
0.9416	High Similarity	NPC78746
0.9379	High Similarity	NPC470264
0.9348	High Similarity	NPC294456
0.9348	High Similarity	NPC212124
0.9348	High Similarity	NPC155963
0.9348	High Similarity	NPC184861
0.9348	High Similarity	NPC225106
0.9348	High Similarity	NPC281014
0.9343	High Similarity	NPC472525
0.9296	High Similarity	NPC469701
0.9296	High Similarity	NPC226722
0.9281	High Similarity	NPC151946
0.9281	High Similarity	NPC211110
0.9275	High Similarity	NPC38099
0.9275	High Similarity	NPC26954
0.927	High Similarity	NPC180716
0.927	High Similarity	NPC62366
0.927	High Similarity	NPC224475
0.927	High Similarity	NPC213173
0.9197	High Similarity	NPC296624
0.9197	High Similarity	NPC471910
0.9197	High Similarity	NPC207002
0.9197	High Similarity	NPC167111
0.9197	High Similarity	NPC133956
0.9197	High Similarity	NPC318400
0.913	High Similarity	NPC326600
0.913	High Similarity	NPC166672
0.913	High Similarity	NPC204353
0.913	High Similarity	NPC267412
0.913	High Similarity	NPC74655
0.913	High Similarity	NPC164269
0.913	High Similarity	NPC260265
0.913	High Similarity	NPC198381
0.913	High Similarity	NPC100986
0.913	High Similarity	NPC50896
0.913	High Similarity	NPC287182
0.913	High Similarity	NPC47163
0.913	High Similarity	NPC127888
0.913	High Similarity	NPC319859
0.913	High Similarity	NPC195343
0.913	High Similarity	NPC18804
0.913	High Similarity	NPC84894
0.9103	High Similarity	NPC96294
0.9103	High Similarity	NPC93924
0.9091	High Similarity	NPC471824
0.9065	High Similarity	NPC471625
0.9065	High Similarity	NPC471909
0.9065	High Similarity	NPC281241
0.9065	High Similarity	NPC33986
0.9065	High Similarity	NPC86892
0.9065	High Similarity	NPC472424
0.9058	High Similarity	NPC31849
0.9058	High Similarity	NPC469449
0.9051	High Similarity	NPC29734
0.9034	High Similarity	NPC52740
0.9	High Similarity	NPC471630
0.9	High Similarity	NPC160727
0.9	High Similarity	NPC55615
0.9	High Similarity	NPC283019
0.9	High Similarity	NPC476455
0.9	High Similarity	NPC177281
0.9	High Similarity	NPC128529
0.9	High Similarity	NPC149320
0.8993	High Similarity	NPC253574
0.8993	High Similarity	NPC98179
0.8986	High Similarity	NPC53587
0.8986	High Similarity	NPC215060
0.8986	High Similarity	NPC169404
0.8986	High Similarity	NPC476352
0.8986	High Similarity	NPC176186
0.898	High Similarity	NPC114740
0.898	High Similarity	NPC107197
0.8978	High Similarity	NPC113098
0.8966	High Similarity	NPC107120
0.8966	High Similarity	NPC74320
0.8926	High Similarity	NPC469699
0.8926	High Similarity	NPC150442
0.8919	High Similarity	NPC213197
0.8913	High Similarity	NPC272650
0.8913	High Similarity	NPC267336
0.8905	High Similarity	NPC295970
0.8904	High Similarity	NPC41844
0.8904	High Similarity	NPC469700
0.8865	High Similarity	NPC166180
0.8857	High Similarity	NPC55149
0.8857	High Similarity	NPC307412
0.8849	High Similarity	NPC14248
0.8849	High Similarity	NPC194277
0.8832	High Similarity	NPC185066
0.8794	High Similarity	NPC185778
0.8794	High Similarity	NPC469675
0.8786	High Similarity	NPC7526
0.8786	High Similarity	NPC222036
0.8784	High Similarity	NPC212670
0.8784	High Similarity	NPC313334
0.8784	High Similarity	NPC206264
0.8768	High Similarity	NPC168710
0.8733	High Similarity	NPC302610
0.8725	High Similarity	NPC100818
0.8725	High Similarity	NPC103116
0.8707	High Similarity	NPC205361
0.8705	High Similarity	NPC474491
0.8705	High Similarity	NPC80170
0.8699	High Similarity	NPC476457
0.8699	High Similarity	NPC471763
0.8696	High Similarity	NPC146540
0.869	High Similarity	NPC84207
0.869	High Similarity	NPC145319
0.869	High Similarity	NPC49542
0.869	High Similarity	NPC128337
0.869	High Similarity	NPC230718
0.869	High Similarity	NPC5253
0.869	High Similarity	NPC139976
0.8686	High Similarity	NPC471826
0.8671	High Similarity	NPC471069
0.8671	High Similarity	NPC124149
0.8671	High Similarity	NPC262328
0.8671	High Similarity	NPC471068
0.8671	High Similarity	NPC87777
0.8658	High Similarity	NPC106138
0.8652	High Similarity	NPC141822
0.8652	High Similarity	NPC142563
0.8652	High Similarity	NPC163557
0.8652	High Similarity	NPC241165
0.8652	High Similarity	NPC469965
0.8652	High Similarity	NPC1220
0.8652	High Similarity	NPC291551
0.8652	High Similarity	NPC205797
0.8649	High Similarity	NPC15577
0.8639	High Similarity	NPC476450
0.8636	High Similarity	NPC173726
0.8636	High Similarity	NPC241600
0.8636	High Similarity	NPC43761
0.863	High Similarity	NPC183646
0.863	High Similarity	NPC119640
0.863	High Similarity	NPC116922
0.8627	High Similarity	NPC17521
0.8627	High Similarity	NPC284810
0.8623	High Similarity	NPC224774
0.8623	High Similarity	NPC121740
0.8623	High Similarity	NPC258567
0.8623	High Similarity	NPC473993
0.8621	High Similarity	NPC279851
0.8621	High Similarity	NPC300611
0.8621	High Similarity	NPC108674
0.8621	High Similarity	NPC472520
0.8621	High Similarity	NPC210192
0.8611	High Similarity	NPC278600
0.8611	High Similarity	NPC35501
0.8611	High Similarity	NPC471072
0.8611	High Similarity	NPC144512
0.8611	High Similarity	NPC37428
0.8611	High Similarity	NPC137262
0.8611	High Similarity	NPC47040
0.8611	High Similarity	NPC471070
0.8611	High Similarity	NPC471071
0.8601	High Similarity	NPC283331
0.8592	High Similarity	NPC131950
0.8591	High Similarity	NPC476348
0.8591	High Similarity	NPC187398
0.8581	High Similarity	NPC474044
0.8581	High Similarity	NPC199928
0.8571	High Similarity	NPC292443
0.8571	High Similarity	NPC177597
0.8571	High Similarity	NPC225445
0.8562	High Similarity	NPC470604
0.8562	High Similarity	NPC470605
0.8562	High Similarity	NPC472353
0.8562	High Similarity	NPC470603
0.8561	High Similarity	NPC199204
0.8561	High Similarity	NPC469453
0.8552	High Similarity	NPC210478
0.8542	High Similarity	NPC131198
0.854	High Similarity	NPC201667
0.854	High Similarity	NPC111347
0.854	High Similarity	NPC73413
0.8531	High Similarity	NPC79957
0.8523	High Similarity	NPC476347
0.8516	High Similarity	NPC470607
0.8511	High Similarity	NPC103799
0.8506	High Similarity	NPC45165
0.8503	High Similarity	NPC469367
0.8497	Intermediate Similarity	NPC268950
0.8497	Intermediate Similarity	NPC108706

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 NPC85624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	903
0.2-0.3	1789
0.3-0.4	2615
0.4-0.5	2015
0.5-0.6	1022
0.6-0.7	308
0.7-0.8	144
0.8-0.85	24
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8784	High Similarity	NPD1653	Approved
0.8652	High Similarity	NPD5123	Clinical (unspecified phase)
0.8652	High Similarity	NPD5124	Phase 1
0.8493	Intermediate Similarity	NPD1652	Phase 2
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1091	Approved
0.8098	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6559	Discontinued
0.8058	Intermediate Similarity	NPD422	Phase 1
0.8025	Intermediate Similarity	NPD8455	Phase 2
0.8025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7962	Intermediate Similarity	NPD6801	Discontinued
0.7949	Intermediate Similarity	NPD4380	Phase 2
0.7867	Intermediate Similarity	NPD7266	Discontinued
0.7823	Intermediate Similarity	NPD1613	Approved
0.7823	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD3818	Discontinued
0.7815	Intermediate Similarity	NPD2424	Discontinued
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7097	Phase 1
0.7771	Intermediate Similarity	NPD7054	Approved
0.7727	Intermediate Similarity	NPD5058	Phase 3
0.7725	Intermediate Similarity	NPD7472	Approved
0.7725	Intermediate Similarity	NPD7074	Phase 3
0.7702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7687	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6797	Phase 2
0.7673	Intermediate Similarity	NPD7411	Suspended
0.7671	Intermediate Similarity	NPD4908	Phase 1
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7647	Intermediate Similarity	NPD6674	Discontinued
0.7643	Intermediate Similarity	NPD5403	Approved
0.7633	Intermediate Similarity	NPD7251	Discontinued
0.7628	Intermediate Similarity	NPD5401	Approved
0.7625	Intermediate Similarity	NPD37	Approved
0.7622	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD4967	Phase 2
0.7593	Intermediate Similarity	NPD4965	Approved
0.7593	Intermediate Similarity	NPD4966	Approved
0.7588	Intermediate Similarity	NPD7808	Phase 3
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6799	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7551	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3817	Phase 2
0.7531	Intermediate Similarity	NPD5402	Approved
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7517	Intermediate Similarity	NPD8651	Approved
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7486	Intermediate Similarity	NPD7583	Approved
0.7484	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD3750	Approved
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7453	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2796	Approved
0.745	Intermediate Similarity	NPD6798	Discontinued
0.745	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7585	Approved
0.7434	Intermediate Similarity	NPD4536	Approved
0.7434	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4538	Approved
0.7432	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2415	Discontinued
0.7419	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6599	Discontinued
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD4625	Phase 3
0.7378	Intermediate Similarity	NPD7768	Phase 2
0.7355	Intermediate Similarity	NPD1549	Phase 2
0.7347	Intermediate Similarity	NPD2797	Approved
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7338	Intermediate Similarity	NPD7843	Approved
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD4749	Approved
0.7326	Intermediate Similarity	NPD7240	Approved
0.7317	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD920	Approved
0.7312	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7157	Approved
0.7303	Intermediate Similarity	NPD4340	Discontinued
0.7303	Intermediate Similarity	NPD6355	Discontinued
0.7299	Intermediate Similarity	NPD2684	Approved
0.729	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5763	Approved
0.729	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5762	Approved
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7283	Intermediate Similarity	NPD7549	Discontinued
0.7279	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6843	Phase 3
0.7273	Intermediate Similarity	NPD5960	Phase 3
0.7273	Intermediate Similarity	NPD5588	Approved
0.7273	Intermediate Similarity	NPD6842	Approved
0.7273	Intermediate Similarity	NPD6841	Approved
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3496	Discontinued
0.7226	Intermediate Similarity	NPD1358	Approved
0.7226	Intermediate Similarity	NPD290	Approved
0.7222	Intermediate Similarity	NPD5691	Approved
0.7219	Intermediate Similarity	NPD3268	Approved
0.7214	Intermediate Similarity	NPD5535	Approved
0.7204	Intermediate Similarity	NPD7584	Approved
0.7197	Intermediate Similarity	NPD1243	Approved
0.7195	Intermediate Similarity	NPD4433	Discontinued
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.7188	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7179	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4626	Approved
0.717	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1510	Phase 2
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD5494	Approved
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4140	Approved
0.7117	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD2935	Discontinued
0.7115	Intermediate Similarity	NPD1551	Phase 2
0.7105	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD8127	Discontinued
0.7097	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD919	Approved
0.708	Intermediate Similarity	NPD9697	Approved
0.7078	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD6667	Approved
0.7063	Intermediate Similarity	NPD6666	Approved
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7055	Intermediate Similarity	NPD5125	Phase 3
0.7055	Intermediate Similarity	NPD5126	Approved
0.7051	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3134	Approved
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3749	Approved
0.7019	Intermediate Similarity	NPD7212	Phase 2
0.7019	Intermediate Similarity	NPD7213	Phase 3
0.7019	Intermediate Similarity	NPD1511	Approved
0.7013	Intermediate Similarity	NPD4307	Phase 2
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD6959	Discontinued
0.7	Intermediate Similarity	NPD3266	Approved
0.6993	Remote Similarity	NPD7985	Registered
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7447	Phase 1
0.6964	Remote Similarity	NPD3882	Suspended
0.6963	Remote Similarity	NPD7783	Phase 2
0.6963	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7229	Phase 3
0.6959	Remote Similarity	NPD3705	Approved
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7435	Discontinued
0.6948	Remote Similarity	NPD4062	Phase 3
0.6944	Remote Similarity	NPD6671	Approved
0.6939	Remote Similarity	NPD1778	Approved
0.6937	Remote Similarity	NPD4535	Phase 3
0.6936	Remote Similarity	NPD7473	Discontinued
0.6933	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6653	Approved
0.6913	Remote Similarity	NPD9717	Approved
0.6909	Remote Similarity	NPD3226	Approved
0.6908	Remote Similarity	NPD3018	Phase 2

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