NPASS Compound

Structure

NPC132078 OpenBabel07101718182D 22 23 0 0 1 0 0 0 0 0999 V2000 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 -2.5981 -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 -0.8660 -1.5000 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 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 11 1 0 0 0 0 5 15 2 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 17 20 1 1 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.17
Volume:	330.619
LogP:	3.648
LogD:	3.421
LogS:	-3.7
# Rotatable Bonds:	8
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.373
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.771
MDCK Permeability:	1.675553539826069e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.84
Human Intestinal Absorption (HIA):	0.056
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	96.16377258300781%
Volume Distribution (VD):	0.943
Pgp-substrate:	1.6894218921661377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.905
CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.406
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	14.626
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.243
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.951
Carcinogencity:	0.183
Eye Corrosion:	0.394
Eye Irritation:	0.983
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC132078

Natural Product ID:	NPC132078
*Common Name:**	(-)-Centrolobol
IUPAC Name:	4-[(5R)-5-hydroxy-7-(4-hydroxyphenyl)heptyl]phenol
Synonyms:	(-)-Centrolobol
Standard InCHIKey:	UYJAYWZGEZOHRU-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C19H24O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h5-6,8-9,11-14,17,20-22H,1-4,7,10H2/t17-/m1/s1
SMILES:	C(CC[C@H](CCc1ccc(cc1)O)O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462922
PubChem CID:	11771038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	Japan	n.a.	PMID[12542351]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20363129]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21550801]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30634	Acer nikoense	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4138	Betula platyphylla	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4138	Betula platyphylla	Species	Betulaceae	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	1
Others	7

Activity Type	# Activity
Cell Line	2
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	19.22	%	PMID[491744]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	31.5	%	PMID[491744]
NPT2	Others	Unspecified		Inhibition	=	-1.3	%	PMID[491743]
NPT2	Others	Unspecified		Inhibition	=	1.3	%	PMID[491743]
NPT2	Others	Unspecified		Inhibition	=	-1.1	%	PMID[491743]
NPT2	Others	Unspecified		Inhibition	=	10.7	%	PMID[491743]
NPT2	Others	Unspecified		Inhibition	=	67.2	%	PMID[491743]
NPT2	Others	Unspecified		IC50	=	73000.0	nM	PMID[491743]

☑ 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 NPC132078 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	236
0.1-0.2	1464
0.2-0.3	4721
0.3-0.4	13283
0.4-0.5	6427
0.5-0.6	9561
0.6-0.7	5293
0.7-0.8	1405
0.8-0.85	201
0.85-0.9	71
0.9-0.95	26
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216468
1.0	High Similarity	NPC51333
1.0	High Similarity	NPC78119
0.9892	High Similarity	NPC213730
0.9787	High Similarity	NPC91461
0.9787	High Similarity	NPC40258
0.9787	High Similarity	NPC7686
0.9565	High Similarity	NPC151715
0.9485	High Similarity	NPC154899
0.9485	High Similarity	NPC233396
0.9474	High Similarity	NPC294741
0.9462	High Similarity	NPC26244
0.9388	High Similarity	NPC135464
0.9388	High Similarity	NPC92623
0.9362	High Similarity	NPC473388
0.9348	High Similarity	NPC45040
0.9247	High Similarity	NPC138117
0.9247	High Similarity	NPC325292
0.9239	High Similarity	NPC300017
0.92	High Similarity	NPC262365
0.9158	High Similarity	NPC216520
0.9158	High Similarity	NPC82664
0.9158	High Similarity	NPC132271
0.9158	High Similarity	NPC292730
0.9149	High Similarity	NPC128062
0.9109	High Similarity	NPC62258
0.9109	High Similarity	NPC55617
0.9053	High Similarity	NPC313650
0.9053	High Similarity	NPC274678
0.9022	High Similarity	NPC104216
0.902	High Similarity	NPC44732
0.902	High Similarity	NPC147634
0.902	High Similarity	NPC63345
0.902	High Similarity	NPC321252
0.902	High Similarity	NPC252544
0.902	High Similarity	NPC120982
0.902	High Similarity	NPC174096
0.902	High Similarity	NPC226401
0.902	High Similarity	NPC79793
0.902	High Similarity	NPC475018
0.899	High Similarity	NPC323810
0.8969	High Similarity	NPC128723
0.8969	High Similarity	NPC92730
0.8947	High Similarity	NPC76938
0.8932	High Similarity	NPC187583
0.8932	High Similarity	NPC257430
0.8932	High Similarity	NPC177576
0.8932	High Similarity	NPC308689
0.8932	High Similarity	NPC179002
0.8925	High Similarity	NPC123273
0.8925	High Similarity	NPC318325
0.8925	High Similarity	NPC280347
0.8925	High Similarity	NPC242240
0.8925	High Similarity	NPC177420
0.8922	High Similarity	NPC306045
0.8922	High Similarity	NPC265211
0.8889	High Similarity	NPC168829
0.8866	High Similarity	NPC474073
0.8866	High Similarity	NPC225464
0.8854	High Similarity	NPC32714
0.8846	High Similarity	NPC153795
0.8846	High Similarity	NPC42911
0.8846	High Similarity	NPC290353
0.883	High Similarity	NPC55561
0.883	High Similarity	NPC300478
0.8817	High Similarity	NPC113460
0.8817	High Similarity	NPC25493
0.8812	High Similarity	NPC113457
0.88	High Similarity	NPC261573
0.88	High Similarity	NPC120693
0.88	High Similarity	NPC288411
0.88	High Similarity	NPC8931
0.8788	High Similarity	NPC471578
0.8788	High Similarity	NPC101025
0.8738	High Similarity	NPC474272
0.8723	High Similarity	NPC258219
0.8713	High Similarity	NPC474839
0.8713	High Similarity	NPC138942
0.871	High Similarity	NPC23167
0.87	High Similarity	NPC135784
0.8696	High Similarity	NPC175313
0.8679	High Similarity	NPC12656
0.8679	High Similarity	NPC473137
0.8679	High Similarity	NPC120280
0.8679	High Similarity	NPC285350
0.8673	High Similarity	NPC201967
0.8667	High Similarity	NPC228425
0.8646	High Similarity	NPC271440
0.8641	High Similarity	NPC317305
0.8632	High Similarity	NPC192
0.8627	High Similarity	NPC188677
0.8614	High Similarity	NPC119860
0.8602	High Similarity	NPC197783
0.8587	High Similarity	NPC265146
0.8586	High Similarity	NPC130193
0.8585	High Similarity	NPC176730
0.8585	High Similarity	NPC123175
0.8557	High Similarity	NPC316301
0.8557	High Similarity	NPC27323
0.8542	High Similarity	NPC304541
0.8542	High Similarity	NPC270547
0.8526	High Similarity	NPC98772
0.8519	High Similarity	NPC473556
0.8519	High Similarity	NPC301651
0.8515	High Similarity	NPC62351
0.8511	High Similarity	NPC184169
0.8495	Intermediate Similarity	NPC248817
0.8491	Intermediate Similarity	NPC228988
0.8485	Intermediate Similarity	NPC32674
0.8476	Intermediate Similarity	NPC183700
0.8462	Intermediate Similarity	NPC61885
0.8462	Intermediate Similarity	NPC11554
0.8462	Intermediate Similarity	NPC75440
0.8462	Intermediate Similarity	NPC63698
0.8462	Intermediate Similarity	NPC201959
0.8454	Intermediate Similarity	NPC306884
0.8454	Intermediate Similarity	NPC162314
0.8454	Intermediate Similarity	NPC94139
0.8454	Intermediate Similarity	NPC3358
0.8454	Intermediate Similarity	NPC210497
0.8454	Intermediate Similarity	NPC147284
0.8447	Intermediate Similarity	NPC70843
0.8447	Intermediate Similarity	NPC95178
0.8447	Intermediate Similarity	NPC29989
0.8447	Intermediate Similarity	NPC271274
0.8447	Intermediate Similarity	NPC69332
0.844	Intermediate Similarity	NPC476266
0.8438	Intermediate Similarity	NPC312304
0.8438	Intermediate Similarity	NPC47950
0.8431	Intermediate Similarity	NPC241891
0.8431	Intermediate Similarity	NPC30506
0.8431	Intermediate Similarity	NPC471511
0.8426	Intermediate Similarity	NPC23402
0.8416	Intermediate Similarity	NPC110764
0.8404	Intermediate Similarity	NPC155393
0.8387	Intermediate Similarity	NPC99482
0.8387	Intermediate Similarity	NPC124436
0.8381	Intermediate Similarity	NPC88141
0.8381	Intermediate Similarity	NPC254833
0.8381	Intermediate Similarity	NPC228343
0.8365	Intermediate Similarity	NPC305603
0.8365	Intermediate Similarity	NPC260952
0.8365	Intermediate Similarity	NPC61033
0.8364	Intermediate Similarity	NPC249435
0.8351	Intermediate Similarity	NPC155908
0.8351	Intermediate Similarity	NPC204210
0.835	Intermediate Similarity	NPC219286
0.835	Intermediate Similarity	NPC239291
0.835	Intermediate Similarity	NPC99557
0.835	Intermediate Similarity	NPC134829
0.8349	Intermediate Similarity	NPC247858
0.8349	Intermediate Similarity	NPC137496
0.8349	Intermediate Similarity	NPC257540
0.8349	Intermediate Similarity	NPC154511
0.8349	Intermediate Similarity	NPC474387
0.8349	Intermediate Similarity	NPC474358
0.8333	Intermediate Similarity	NPC68269
0.8333	Intermediate Similarity	NPC471228
0.8333	Intermediate Similarity	NPC235762
0.8317	Intermediate Similarity	NPC174911
0.8317	Intermediate Similarity	NPC225506
0.8316	Intermediate Similarity	NPC307235
0.8316	Intermediate Similarity	NPC407
0.8302	Intermediate Similarity	NPC296683
0.83	Intermediate Similarity	NPC77492
0.8288	Intermediate Similarity	NPC182240
0.8288	Intermediate Similarity	NPC470215
0.8288	Intermediate Similarity	NPC470214
0.8288	Intermediate Similarity	NPC109371
0.8286	Intermediate Similarity	NPC206341
0.8283	Intermediate Similarity	NPC286006
0.8283	Intermediate Similarity	NPC8392
0.828	Intermediate Similarity	NPC304538
0.8273	Intermediate Similarity	NPC610
0.8273	Intermediate Similarity	NPC200988
0.8273	Intermediate Similarity	NPC175799
0.8273	Intermediate Similarity	NPC145023
0.8273	Intermediate Similarity	NPC477136
0.8269	Intermediate Similarity	NPC118286
0.8269	Intermediate Similarity	NPC470700
0.8269	Intermediate Similarity	NPC302681
0.8269	Intermediate Similarity	NPC248904
0.8269	Intermediate Similarity	NPC109691
0.8269	Intermediate Similarity	NPC39664
0.8269	Intermediate Similarity	NPC39097
0.8269	Intermediate Similarity	NPC54765
0.8261	Intermediate Similarity	NPC283012
0.8261	Intermediate Similarity	NPC475199
0.8257	Intermediate Similarity	NPC147179
0.8252	Intermediate Similarity	NPC475225
0.8252	Intermediate Similarity	NPC254965
0.8252	Intermediate Similarity	NPC12278
0.8252	Intermediate Similarity	NPC327811
0.8241	Intermediate Similarity	NPC35344
0.8241	Intermediate Similarity	NPC471485
0.8241	Intermediate Similarity	NPC141003
0.8241	Intermediate Similarity	NPC261343
0.8235	Intermediate Similarity	NPC12221
0.8235	Intermediate Similarity	NPC143659
0.8235	Intermediate Similarity	NPC51015

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 NPC132078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	958
0.2-0.3	1220
0.3-0.4	2814
0.4-0.5	2052
0.5-0.6	1186
0.6-0.7	549
0.7-0.8	102
0.8-0.85	11
0.85-0.9	0
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9462	High Similarity	NPD2859	Approved
0.9462	High Similarity	NPD2860	Approved
0.9355	High Similarity	NPD2933	Approved
0.9355	High Similarity	NPD2934	Approved
0.9167	High Similarity	NPD3020	Approved
0.8557	High Similarity	NPD1432	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD111	Approved
0.8381	Intermediate Similarity	NPD3021	Approved
0.8381	Intermediate Similarity	NPD3022	Approved
0.8235	Intermediate Similarity	NPD940	Approved
0.8235	Intermediate Similarity	NPD846	Approved
0.8214	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD3091	Approved
0.8137	Intermediate Similarity	NPD3028	Approved
0.8137	Intermediate Similarity	NPD1242	Phase 1
0.81	Intermediate Similarity	NPD1809	Phase 2
0.81	Intermediate Similarity	NPD844	Approved
0.8081	Intermediate Similarity	NPD845	Approved
0.8037	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD2684	Approved
0.7931	Intermediate Similarity	NPD4659	Approved
0.7925	Intermediate Similarity	NPD968	Approved
0.7913	Intermediate Similarity	NPD3092	Approved
0.7909	Intermediate Similarity	NPD2228	Approved
0.7909	Intermediate Similarity	NPD2234	Approved
0.7909	Intermediate Similarity	NPD2229	Approved
0.7845	Intermediate Similarity	NPD2561	Approved
0.7845	Intermediate Similarity	NPD2562	Approved
0.7843	Intermediate Similarity	NPD288	Approved
0.7797	Intermediate Similarity	NPD4103	Phase 2
0.7797	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD3095	Discontinued
0.7727	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD9294	Approved
0.7706	Intermediate Similarity	NPD5451	Approved
0.7685	Intermediate Similarity	NPD2342	Discontinued
0.7658	Intermediate Similarity	NPD7635	Approved
0.7658	Intermediate Similarity	NPD7843	Approved
0.7647	Intermediate Similarity	NPD3094	Phase 2
0.7642	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD16	Approved
0.7632	Intermediate Similarity	NPD856	Approved
0.7627	Intermediate Similarity	NPD6582	Phase 2
0.7627	Intermediate Similarity	NPD6583	Phase 3
0.7607	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6516	Phase 2
0.7586	Intermediate Similarity	NPD5846	Approved
0.757	Intermediate Similarity	NPD9608	Approved
0.757	Intermediate Similarity	NPD9610	Approved
0.7565	Intermediate Similarity	NPD5303	Approved
0.7565	Intermediate Similarity	NPD5304	Approved
0.7565	Intermediate Similarity	NPD1548	Phase 1
0.7545	Intermediate Similarity	NPD1792	Phase 2
0.7545	Intermediate Similarity	NPD4750	Phase 3
0.7541	Intermediate Similarity	NPD3027	Phase 3
0.7521	Intermediate Similarity	NPD2861	Phase 2
0.7521	Intermediate Similarity	NPD3421	Phase 3
0.75	Intermediate Similarity	NPD4093	Discontinued
0.7479	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD317	Approved
0.7478	Intermediate Similarity	NPD318	Approved
0.7458	Intermediate Similarity	NPD1610	Phase 2
0.7456	Intermediate Similarity	NPD7157	Approved
0.7438	Intermediate Similarity	NPD6584	Phase 3
0.7436	Intermediate Similarity	NPD4059	Approved
0.7436	Intermediate Similarity	NPD2286	Discontinued
0.7436	Intermediate Similarity	NPD4589	Approved
0.7436	Intermediate Similarity	NPD2932	Approved
0.7436	Intermediate Similarity	NPD3019	Approved
0.7434	Intermediate Similarity	NPD5283	Phase 1
0.7431	Intermediate Similarity	NPD1444	Approved
0.7431	Intermediate Similarity	NPD1445	Approved
0.7419	Intermediate Similarity	NPD6407	Approved
0.7419	Intermediate Similarity	NPD6405	Approved
0.7411	Intermediate Similarity	NPD228	Approved
0.7407	Intermediate Similarity	NPD1237	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7377	Intermediate Similarity	NPD5736	Approved
0.7373	Intermediate Similarity	NPD3847	Discontinued
0.7368	Intermediate Similarity	NPD9618	Approved
0.7368	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9614	Approved
0.7364	Intermediate Similarity	NPD290	Approved
0.7364	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD821	Approved
0.7345	Intermediate Similarity	NPD5535	Approved
0.7317	Intermediate Similarity	NPD4908	Phase 1
0.7304	Intermediate Similarity	NPD6671	Approved
0.7288	Intermediate Similarity	NPD9381	Approved
0.7288	Intermediate Similarity	NPD2668	Approved
0.7288	Intermediate Similarity	NPD9384	Approved
0.7288	Intermediate Similarity	NPD2667	Approved
0.7281	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1894	Discontinued
0.7264	Intermediate Similarity	NPD9273	Approved
0.7263	Intermediate Similarity	NPD9088	Approved
0.725	Intermediate Similarity	NPD2231	Phase 2
0.725	Intermediate Similarity	NPD2235	Phase 2
0.7241	Intermediate Similarity	NPD3596	Phase 2
0.7222	Intermediate Similarity	NPD3059	Approved
0.7222	Intermediate Similarity	NPD3061	Approved
0.7222	Intermediate Similarity	NPD3062	Approved
0.7213	Intermediate Similarity	NPD1135	Approved
0.7213	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1129	Approved
0.7213	Intermediate Similarity	NPD1133	Approved
0.7213	Intermediate Similarity	NPD1134	Approved
0.7213	Intermediate Similarity	NPD1131	Approved
0.72	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9377	Approved
0.7193	Intermediate Similarity	NPD9379	Approved
0.719	Intermediate Similarity	NPD3685	Discontinued
0.7188	Intermediate Similarity	NPD3553	Approved
0.7188	Intermediate Similarity	NPD3552	Approved
0.7188	Intermediate Similarity	NPD3554	Approved
0.7188	Intermediate Similarity	NPD3555	Approved
0.7179	Intermediate Similarity	NPD9613	Approved
0.7179	Intermediate Similarity	NPD9615	Approved
0.7179	Intermediate Similarity	NPD9616	Approved
0.7168	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD256	Approved
0.7155	Intermediate Similarity	NPD255	Approved
0.7143	Intermediate Similarity	NPD6663	Approved
0.7143	Intermediate Similarity	NPD1751	Approved
0.7131	Intermediate Similarity	NPD5310	Approved
0.7131	Intermediate Similarity	NPD5311	Approved
0.7119	Intermediate Similarity	NPD6580	Approved
0.7119	Intermediate Similarity	NPD316	Approved
0.7119	Intermediate Similarity	NPD6581	Approved
0.7119	Intermediate Similarity	NPD7330	Discontinued
0.7117	Intermediate Similarity	NPD3134	Approved
0.7109	Intermediate Similarity	NPD3052	Approved
0.7109	Intermediate Similarity	NPD5314	Approved
0.7109	Intermediate Similarity	NPD2568	Approved
0.7109	Intermediate Similarity	NPD3054	Approved
0.7103	Intermediate Similarity	NPD9495	Approved
0.7094	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4060	Phase 1
0.7087	Intermediate Similarity	NPD1613	Approved
0.7087	Intermediate Similarity	NPD3620	Phase 2
0.7073	Intermediate Similarity	NPD3055	Approved
0.7073	Intermediate Similarity	NPD3053	Approved
0.7063	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD1357	Approved
0.7059	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD9622	Approved
0.7025	Intermediate Similarity	NPD1535	Discovery
0.7016	Intermediate Similarity	NPD7451	Discontinued
0.7009	Intermediate Similarity	NPD2557	Approved
0.7	Intermediate Similarity	NPD9500	Approved
0.7	Intermediate Similarity	NPD4658	Approved
0.7	Intermediate Similarity	NPD4656	Approved
0.7	Intermediate Similarity	NPD7743	Approved
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD7742	Approved
0.6992	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6179	Discontinued
0.6975	Remote Similarity	NPD9545	Approved
0.6975	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2553	Approved
0.6972	Remote Similarity	NPD2549	Approved
0.6972	Remote Similarity	NPD2550	Approved
0.6972	Remote Similarity	NPD2552	Approved
0.6972	Remote Similarity	NPD2558	Approved
0.6972	Remote Similarity	NPD2555	Approved
0.697	Remote Similarity	NPD9089	Approved
0.6967	Remote Similarity	NPD1481	Phase 2
0.6967	Remote Similarity	NPD2232	Approved
0.6967	Remote Similarity	NPD2230	Approved
0.6967	Remote Similarity	NPD2233	Approved
0.6953	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2238	Phase 2
0.6953	Remote Similarity	NPD4140	Approved
0.6949	Remote Similarity	NPD9568	Approved
0.6944	Remote Similarity	NPD9611	Approved
0.6944	Remote Similarity	NPD9612	Approved
0.6944	Remote Similarity	NPD9609	Approved
0.6935	Remote Similarity	NPD1164	Approved
0.6929	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD475	Phase 2
0.6923	Remote Similarity	NPD1793	Approved
0.6923	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1791	Approved
0.6923	Remote Similarity	NPD4536	Approved
0.6923	Remote Similarity	NPD2629	Approved
0.6923	Remote Similarity	NPD4538	Approved
0.6917	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1651	Approved
0.6911	Remote Similarity	NPD5327	Phase 3
0.6911	Remote Similarity	NPD1669	Approved
0.6909	Remote Similarity	NPD854	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