NPASS Compound

Structure

CID7686 OpenBabel06191715332D 23 24 0 0 1 0 0 0 0 0999 V2000 5.1962 0.0000 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 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 6.9282 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 6.9282 -1.0000 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 6.0622 -2.5000 0.0000 O 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 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 1 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 6 0 0 0 19 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.17
Volume:	339.409
LogP:	2.69
LogD:	2.76
LogS:	-3.32
# Rotatable Bonds:	8
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	2.768
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.994
MDCK Permeability:	6.792166914237896e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.168
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	93.08442687988281%
Volume Distribution (VD):	1.063
Pgp-substrate:	6.722781181335449%

ADMET: Metabolism

CYP1A2-inhibitor:	0.609
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.741
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.288
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	14.887
Half-life (T1/2):	0.919

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.952
Carcinogencity:	0.393
Eye Corrosion:	0.251
Eye Irritation:	0.966
Respiratory Toxicity:	0.432

Download Data

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

Natural Product: NPC7686

Natural Product ID:	NPC7686
*Common Name:**	(3S,5R)-1,7-Bis(4-Hydroxyphenyl)Heptane-3,5-Diol
IUPAC Name:	(3S,5R)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol
Synonyms:
Standard InCHIKey:	GZVIQGVWSNEONZ-KDURUIRLSA-N
Standard InCHI:	InChI=1S/C19H24O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-4,7-10,18-23H,5-6,11-13H2/t18-,19+
SMILES:	O[C@H](C[C@@H](CCc1ccc(cc1)O)O)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1824579
PubChem CID:	25763835
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15361	Alnus japonica	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[540412]

☑ 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 NPC7686 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	238
0.1-0.2	1336
0.2-0.3	4383
0.3-0.4	13247
0.4-0.5	6365
0.5-0.6	9332
0.6-0.7	5873
0.7-0.8	1636
0.8-0.85	195
0.85-0.9	65
0.9-0.95	19
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC91461
1.0	High Similarity	NPC40258
0.9894	High Similarity	NPC213730
0.9787	High Similarity	NPC51333
0.9787	High Similarity	NPC78119
0.9787	High Similarity	NPC132078
0.9787	High Similarity	NPC216468
0.949	High Similarity	NPC233396
0.949	High Similarity	NPC154899
0.9394	High Similarity	NPC92623
0.9394	High Similarity	NPC135464
0.9362	High Similarity	NPC151715
0.9278	High Similarity	NPC294741
0.9263	High Similarity	NPC26244
0.9216	High Similarity	NPC63345
0.9216	High Similarity	NPC475018
0.9167	High Similarity	NPC473388
0.9149	High Similarity	NPC45040
0.9126	High Similarity	NPC187583
0.9126	High Similarity	NPC179002
0.9126	High Similarity	NPC257430
0.9053	High Similarity	NPC138117
0.9053	High Similarity	NPC325292
0.9043	High Similarity	NPC300017
0.9038	High Similarity	NPC153795
0.9038	High Similarity	NPC42911
0.9038	High Similarity	NPC290353
0.9029	High Similarity	NPC147634
0.9029	High Similarity	NPC79793
0.9029	High Similarity	NPC44732
0.9029	High Similarity	NPC120982
0.9029	High Similarity	NPC226401
0.9029	High Similarity	NPC174096
0.902	High Similarity	NPC262365
0.9	High Similarity	NPC323810
0.8969	High Similarity	NPC216520
0.8969	High Similarity	NPC132271
0.8969	High Similarity	NPC82664
0.8969	High Similarity	NPC292730
0.8958	High Similarity	NPC128062
0.8942	High Similarity	NPC177576
0.8942	High Similarity	NPC308689
0.8932	High Similarity	NPC55617
0.8932	High Similarity	NPC62258
0.8932	High Similarity	NPC474272
0.8868	High Similarity	NPC473137
0.8866	High Similarity	NPC313650
0.8866	High Similarity	NPC274678
0.8846	High Similarity	NPC321252
0.8846	High Similarity	NPC252544
0.883	High Similarity	NPC104216
0.8788	High Similarity	NPC92730
0.8788	High Similarity	NPC128723
0.8763	High Similarity	NPC76938
0.875	High Similarity	NPC306045
0.875	High Similarity	NPC265211
0.8737	High Similarity	NPC177420
0.8737	High Similarity	NPC242240
0.8737	High Similarity	NPC280347
0.8737	High Similarity	NPC318325
0.8737	High Similarity	NPC123273
0.8725	High Similarity	NPC474839
0.8713	High Similarity	NPC168829
0.8704	High Similarity	NPC301651
0.8704	High Similarity	NPC473556
0.8692	High Similarity	NPC12656
0.8692	High Similarity	NPC120280
0.8692	High Similarity	NPC285350
0.8687	High Similarity	NPC474073
0.8687	High Similarity	NPC225464
0.8673	High Similarity	NPC32714
0.8646	High Similarity	NPC300478
0.8646	High Similarity	NPC55561
0.8641	High Similarity	NPC113457
0.8641	High Similarity	NPC188677
0.8632	High Similarity	NPC113460
0.8632	High Similarity	NPC25493
0.8627	High Similarity	NPC288411
0.8627	High Similarity	NPC119860
0.8627	High Similarity	NPC120693
0.8627	High Similarity	NPC261573
0.8627	High Similarity	NPC8931
0.8624	High Similarity	NPC476266
0.8614	High Similarity	NPC471578
0.8614	High Similarity	NPC101025
0.86	High Similarity	NPC130193
0.8544	High Similarity	NPC138942
0.8542	High Similarity	NPC258219
0.8529	High Similarity	NPC135784
0.8526	High Similarity	NPC23167
0.8511	High Similarity	NPC175313
0.8505	High Similarity	NPC228425
0.85	High Similarity	NPC201967
0.8491	Intermediate Similarity	NPC183700
0.8476	Intermediate Similarity	NPC63698
0.8476	Intermediate Similarity	NPC61885
0.8476	Intermediate Similarity	NPC317305
0.8469	Intermediate Similarity	NPC271440
0.8468	Intermediate Similarity	NPC470214
0.8468	Intermediate Similarity	NPC470215
0.8468	Intermediate Similarity	NPC109371
0.8462	Intermediate Similarity	NPC39664
0.8462	Intermediate Similarity	NPC109691
0.8462	Intermediate Similarity	NPC118286
0.8462	Intermediate Similarity	NPC470700
0.8462	Intermediate Similarity	NPC302681
0.8462	Intermediate Similarity	NPC39097
0.8462	Intermediate Similarity	NPC70843
0.8454	Intermediate Similarity	NPC192
0.8454	Intermediate Similarity	NPC47950
0.8447	Intermediate Similarity	NPC30506
0.8447	Intermediate Similarity	NPC471511
0.8447	Intermediate Similarity	NPC241891
0.844	Intermediate Similarity	NPC23402
0.8426	Intermediate Similarity	NPC123175
0.8426	Intermediate Similarity	NPC261343
0.8426	Intermediate Similarity	NPC176730
0.8421	Intermediate Similarity	NPC197783
0.8404	Intermediate Similarity	NPC99482
0.8404	Intermediate Similarity	NPC265146
0.8396	Intermediate Similarity	NPC228343
0.8396	Intermediate Similarity	NPC254833
0.8396	Intermediate Similarity	NPC88141
0.8393	Intermediate Similarity	NPC223451
0.8384	Intermediate Similarity	NPC27323
0.8384	Intermediate Similarity	NPC316301
0.8381	Intermediate Similarity	NPC54844
0.8381	Intermediate Similarity	NPC305603
0.8381	Intermediate Similarity	NPC61033
0.8378	Intermediate Similarity	NPC86198
0.8367	Intermediate Similarity	NPC304541
0.8367	Intermediate Similarity	NPC270547
0.8365	Intermediate Similarity	NPC134829
0.8365	Intermediate Similarity	NPC246056
0.8351	Intermediate Similarity	NPC98772
0.835	Intermediate Similarity	NPC68269
0.835	Intermediate Similarity	NPC62351
0.8333	Intermediate Similarity	NPC184169
0.8333	Intermediate Similarity	NPC228988
0.8333	Intermediate Similarity	NPC43525
0.8319	Intermediate Similarity	NPC469703
0.8319	Intermediate Similarity	NPC469704
0.8319	Intermediate Similarity	NPC201402
0.8319	Intermediate Similarity	NPC160854
0.8317	Intermediate Similarity	NPC32674
0.8316	Intermediate Similarity	NPC248817
0.8304	Intermediate Similarity	NPC70084
0.8304	Intermediate Similarity	NPC182240
0.8304	Intermediate Similarity	NPC151197
0.8302	Intermediate Similarity	NPC75440
0.8302	Intermediate Similarity	NPC201959
0.8302	Intermediate Similarity	NPC11554
0.8288	Intermediate Similarity	NPC145023
0.8288	Intermediate Similarity	NPC175799
0.8288	Intermediate Similarity	NPC200988
0.8288	Intermediate Similarity	NPC610
0.8286	Intermediate Similarity	NPC271274
0.8286	Intermediate Similarity	NPC95178
0.8286	Intermediate Similarity	NPC69332
0.8286	Intermediate Similarity	NPC29989
0.8286	Intermediate Similarity	NPC248904
0.8283	Intermediate Similarity	NPC162314
0.8283	Intermediate Similarity	NPC94139
0.8283	Intermediate Similarity	NPC3358
0.8283	Intermediate Similarity	NPC306884
0.8283	Intermediate Similarity	NPC147284
0.8283	Intermediate Similarity	NPC210497
0.8273	Intermediate Similarity	NPC474486
0.8265	Intermediate Similarity	NPC312304
0.8257	Intermediate Similarity	NPC471485
0.8252	Intermediate Similarity	NPC110764
0.8252	Intermediate Similarity	NPC100340
0.8252	Intermediate Similarity	NPC143659
0.8246	Intermediate Similarity	NPC473853
0.8246	Intermediate Similarity	NPC324571
0.8246	Intermediate Similarity	NPC54872
0.8246	Intermediate Similarity	NPC113865
0.8246	Intermediate Similarity	NPC262156
0.8246	Intermediate Similarity	NPC470212
0.8246	Intermediate Similarity	NPC469686
0.8246	Intermediate Similarity	NPC312675
0.8246	Intermediate Similarity	NPC184651
0.8246	Intermediate Similarity	NPC343720
0.8241	Intermediate Similarity	NPC225679
0.8241	Intermediate Similarity	NPC476632
0.8241	Intermediate Similarity	NPC165770
0.8241	Intermediate Similarity	NPC4493
0.823	Intermediate Similarity	NPC473136
0.823	Intermediate Similarity	NPC34634
0.823	Intermediate Similarity	NPC265454
0.8229	Intermediate Similarity	NPC155393
0.8214	Intermediate Similarity	NPC249435
0.8214	Intermediate Similarity	NPC474214
0.8211	Intermediate Similarity	NPC124436
0.8208	Intermediate Similarity	NPC260952
0.8198	Intermediate Similarity	NPC474358
0.8198	Intermediate Similarity	NPC257540
0.8198	Intermediate Similarity	NPC154511
0.8198	Intermediate Similarity	NPC137496
0.8198	Intermediate Similarity	NPC474387

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 NPC7686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	898
0.2-0.3	1325
0.3-0.4	2799
0.4-0.5	2019
0.5-0.6	1219
0.6-0.7	544
0.7-0.8	98
0.8-0.85	7
0.85-0.9	1
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9263	High Similarity	NPD2860	Approved
0.9263	High Similarity	NPD2859	Approved
0.9158	High Similarity	NPD2933	Approved
0.9158	High Similarity	NPD2934	Approved
0.898	High Similarity	NPD3020	Approved
0.8396	Intermediate Similarity	NPD3022	Approved
0.8396	Intermediate Similarity	NPD3021	Approved
0.8384	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD846	Approved
0.8252	Intermediate Similarity	NPD940	Approved
0.8211	Intermediate Similarity	NPD111	Approved
0.8155	Intermediate Similarity	NPD1242	Phase 1
0.8155	Intermediate Similarity	NPD3028	Approved
0.807	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD3091	Approved
0.7941	Intermediate Similarity	NPD844	Approved
0.7941	Intermediate Similarity	NPD1809	Phase 2
0.7921	Intermediate Similarity	NPD845	Approved
0.789	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3094	Phase 2
0.7798	Intermediate Similarity	NPD2684	Approved
0.7797	Intermediate Similarity	NPD4659	Approved
0.7778	Intermediate Similarity	NPD3092	Approved
0.7778	Intermediate Similarity	NPD968	Approved
0.7768	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD2229	Approved
0.7768	Intermediate Similarity	NPD2228	Approved
0.7768	Intermediate Similarity	NPD2234	Approved
0.7759	Intermediate Similarity	NPD3095	Discontinued
0.7748	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2561	Approved
0.7712	Intermediate Similarity	NPD2562	Approved
0.7705	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD288	Approved
0.7679	Intermediate Similarity	NPD7843	Approved
0.7667	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4103	Phase 2
0.7642	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1548	Phase 1
0.7581	Intermediate Similarity	NPD6405	Approved
0.7581	Intermediate Similarity	NPD6407	Approved
0.7568	Intermediate Similarity	NPD5451	Approved
0.7568	Intermediate Similarity	NPD4750	Phase 3
0.7553	Intermediate Similarity	NPD9294	Approved
0.7545	Intermediate Similarity	NPD2342	Discontinued
0.7522	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD16	Approved
0.75	Intermediate Similarity	NPD856	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6583	Phase 3
0.75	Intermediate Similarity	NPD6582	Phase 2
0.748	Intermediate Similarity	NPD4908	Phase 1
0.7479	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD1610	Phase 2
0.7479	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7157	Approved
0.7458	Intermediate Similarity	NPD5846	Approved
0.7458	Intermediate Similarity	NPD6516	Phase 2
0.7456	Intermediate Similarity	NPD5283	Phase 1
0.7436	Intermediate Similarity	NPD5304	Approved
0.7436	Intermediate Similarity	NPD5303	Approved
0.7431	Intermediate Similarity	NPD9608	Approved
0.7431	Intermediate Similarity	NPD9610	Approved
0.7411	Intermediate Similarity	NPD1792	Phase 2
0.7398	Intermediate Similarity	NPD2861	Phase 2
0.7395	Intermediate Similarity	NPD3421	Phase 3
0.7395	Intermediate Similarity	NPD3847	Discontinued
0.7387	Intermediate Similarity	NPD290	Approved
0.7373	Intermediate Similarity	NPD4093	Discontinued
0.7368	Intermediate Similarity	NPD5535	Approved
0.736	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD318	Approved
0.735	Intermediate Similarity	NPD317	Approved
0.7317	Intermediate Similarity	NPD6584	Phase 3
0.7311	Intermediate Similarity	NPD4589	Approved
0.7311	Intermediate Similarity	NPD2932	Approved
0.7311	Intermediate Similarity	NPD2286	Discontinued
0.7311	Intermediate Similarity	NPD3019	Approved
0.7311	Intermediate Similarity	NPD4059	Approved
0.7304	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1445	Approved
0.7297	Intermediate Similarity	NPD1444	Approved
0.729	Intermediate Similarity	NPD9273	Approved
0.7281	Intermediate Similarity	NPD228	Approved
0.7273	Intermediate Similarity	NPD1237	Approved
0.7266	Intermediate Similarity	NPD2568	Approved
0.7258	Intermediate Similarity	NPD5736	Approved
0.7244	Intermediate Similarity	NPD3059	Approved
0.7244	Intermediate Similarity	NPD3062	Approved
0.7244	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3061	Approved
0.7244	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD9618	Approved
0.7241	Intermediate Similarity	NPD9614	Approved
0.7241	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1134	Approved
0.7236	Intermediate Similarity	NPD1131	Approved
0.7236	Intermediate Similarity	NPD1135	Approved
0.7236	Intermediate Similarity	NPD1129	Approved
0.7236	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1133	Approved
0.7234	Intermediate Similarity	NPD9087	Approved
0.7232	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD821	Approved
0.7213	Intermediate Similarity	NPD3685	Discontinued
0.7209	Intermediate Similarity	NPD3555	Approved
0.7209	Intermediate Similarity	NPD3553	Approved
0.7209	Intermediate Similarity	NPD3554	Approved
0.7209	Intermediate Similarity	NPD3552	Approved
0.7179	Intermediate Similarity	NPD6671	Approved
0.7167	Intermediate Similarity	NPD9381	Approved
0.7167	Intermediate Similarity	NPD2667	Approved
0.7167	Intermediate Similarity	NPD2668	Approved
0.7167	Intermediate Similarity	NPD9384	Approved
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7132	Intermediate Similarity	NPD5314	Approved
0.7131	Intermediate Similarity	NPD2231	Phase 2
0.7131	Intermediate Similarity	NPD2235	Phase 2
0.7119	Intermediate Similarity	NPD3596	Phase 2
0.7119	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD9088	Approved
0.7109	Intermediate Similarity	NPD4060	Phase 1
0.7087	Intermediate Similarity	NPD6798	Discontinued
0.7077	Intermediate Similarity	NPD4536	Approved
0.7077	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4538	Approved
0.7073	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9377	Approved
0.7069	Intermediate Similarity	NPD9379	Approved
0.7059	Intermediate Similarity	NPD9613	Approved
0.7059	Intermediate Similarity	NPD9616	Approved
0.7059	Intermediate Similarity	NPD9615	Approved
0.7054	Intermediate Similarity	NPD5048	Discontinued
0.7049	Intermediate Similarity	NPD1091	Approved
0.7049	Intermediate Similarity	NPD1535	Discovery
0.7045	Intermediate Similarity	NPD7266	Discontinued
0.7043	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7451	Discontinued
0.7034	Intermediate Similarity	NPD255	Approved
0.7034	Intermediate Similarity	NPD256	Approved
0.7031	Intermediate Similarity	NPD6663	Approved
0.7031	Intermediate Similarity	NPD6233	Phase 2
0.7025	Intermediate Similarity	NPD1751	Approved
0.7023	Intermediate Similarity	NPD5960	Phase 3
0.7023	Intermediate Similarity	NPD5588	Approved
0.7016	Intermediate Similarity	NPD5311	Approved
0.7016	Intermediate Similarity	NPD5310	Approved
0.7015	Intermediate Similarity	NPD3400	Discontinued
0.7008	Intermediate Similarity	NPD3136	Phase 2
0.7	Intermediate Similarity	NPD6581	Approved
0.7	Intermediate Similarity	NPD316	Approved
0.7	Intermediate Similarity	NPD3052	Approved
0.7	Intermediate Similarity	NPD6580	Approved
0.7	Intermediate Similarity	NPD7330	Discontinued
0.7	Intermediate Similarity	NPD3054	Approved
0.7	Intermediate Similarity	NPD9089	Approved
0.6992	Remote Similarity	NPD1481	Phase 2
0.6991	Remote Similarity	NPD3134	Approved
0.6977	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD3620	Phase 2
0.6977	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9495	Approved
0.696	Remote Similarity	NPD3053	Approved
0.696	Remote Similarity	NPD1164	Approved
0.696	Remote Similarity	NPD3055	Approved
0.6953	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD475	Phase 2
0.6947	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1357	Approved
0.6935	Remote Similarity	NPD9622	Approved
0.693	Remote Similarity	NPD1358	Approved
0.693	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD3690	Phase 2
0.6905	Remote Similarity	NPD3691	Phase 2
0.69	Remote Similarity	NPD9093	Approved
0.6899	Remote Similarity	NPD4062	Phase 3
0.6897	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7033	Discontinued
0.6894	Remote Similarity	NPD7743	Approved
0.6894	Remote Similarity	NPD7742	Approved
0.6891	Remote Similarity	NPD2557	Approved
0.6885	Remote Similarity	NPD4626	Approved
0.688	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4658	Approved
0.6875	Remote Similarity	NPD9500	Approved
0.6875	Remote Similarity	NPD4656	Approved
0.6875	Remote Similarity	NPD6179	Discontinued
0.686	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7741	Discontinued
0.686	Remote Similarity	NPD1759	Phase 1
0.686	Remote Similarity	NPD9545	Approved
0.6855	Remote Similarity	NPD2233	Approved
0.6855	Remote Similarity	NPD2232	Approved
0.6855	Remote Similarity	NPD2230	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