NPASS Compound

Structure

CID213730 OpenBabel06191716002D 22 23 0 0 1 0 0 0 0 0999 V2000 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -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 8.6603 -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 7.7942 -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 -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 7.7942 -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 -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 2 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 -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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 15 2 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 1 0 0 0 19 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.17
Volume:	330.619
LogP:	3.121
LogD:	2.92
LogS:	-4.16
# 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:	0.702
Synthetic Accessibility Score:	2.648
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:	-4.972
MDCK Permeability:	6.740949174854904e-06
Pgp-inhibitor:	0.015
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.099
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.805
Plasma Protein Binding (PPB):	94.68131256103516%
Volume Distribution (VD):	1.123
Pgp-substrate:	2.275272846221924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.755
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.952
CYP2C19-substrate:	0.169
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.429
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	14.439
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.286
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.944
Carcinogencity:	0.311
Eye Corrosion:	0.333
Eye Irritation:	0.979
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC213730

Natural Product ID:	NPC213730
*Common Name:**	(3R,5R)-1-(4-Hydroxyphenyl)-7-Phenylheptane-3,5-Diol
IUPAC Name:	(3R,5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol
Synonyms:
Standard InCHIKey:	GIJBVGHAAVSQGB-RTBURBONSA-N
Standard InCHI:	InChI=1S/C19H24O3/c20-17-10-6-16(7-11-17)9-13-19(22)14-18(21)12-8-15-4-2-1-3-5-15/h1-7,10-11,18-22H,8-9,12-14H2/t18-,19-/m1/s1
SMILES:	c1ccc(cc1)CC[C@H](C[C@@H](CCc1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489757
PubChem CID:	13888136
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
NPO33450	aplinia officinarum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12350154]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT673	Organism	Gallus gallus	Gallus gallus	Inhibition	=	37.7	%	PMID[453569]

☑ 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 NPC213730 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	241
0.1-0.2	1391
0.2-0.3	4621
0.3-0.4	13355
0.4-0.5	6259
0.5-0.6	9501
0.6-0.7	5516
0.7-0.8	1504
0.8-0.85	208
0.85-0.9	70
0.9-0.95	23
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC40258
0.9894	High Similarity	NPC7686
0.9894	High Similarity	NPC91461
0.9892	High Similarity	NPC78119
0.9892	High Similarity	NPC51333
0.9892	High Similarity	NPC216468
0.9892	High Similarity	NPC132078
0.9588	High Similarity	NPC154899
0.9588	High Similarity	NPC233396
0.949	High Similarity	NPC92623
0.949	High Similarity	NPC135464
0.9462	High Similarity	NPC151715
0.9375	High Similarity	NPC294741
0.9362	High Similarity	NPC26244
0.9263	High Similarity	NPC473388
0.9247	High Similarity	NPC45040
0.9149	High Similarity	NPC325292
0.9149	High Similarity	NPC138117
0.914	High Similarity	NPC300017
0.9118	High Similarity	NPC63345
0.9118	High Similarity	NPC475018
0.9109	High Similarity	NPC262365
0.9062	High Similarity	NPC216520
0.9062	High Similarity	NPC292730
0.9062	High Similarity	NPC82664
0.9062	High Similarity	NPC132271
0.9053	High Similarity	NPC128062
0.9029	High Similarity	NPC179002
0.9029	High Similarity	NPC257430
0.9029	High Similarity	NPC187583
0.902	High Similarity	NPC62258
0.902	High Similarity	NPC55617
0.8958	High Similarity	NPC313650
0.8958	High Similarity	NPC274678
0.8942	High Similarity	NPC42911
0.8942	High Similarity	NPC153795
0.8942	High Similarity	NPC290353
0.8932	High Similarity	NPC252544
0.8932	High Similarity	NPC44732
0.8932	High Similarity	NPC226401
0.8932	High Similarity	NPC147634
0.8932	High Similarity	NPC321252
0.8932	High Similarity	NPC120982
0.8932	High Similarity	NPC174096
0.8932	High Similarity	NPC79793
0.8925	High Similarity	NPC104216
0.89	High Similarity	NPC323810
0.8878	High Similarity	NPC128723
0.8878	High Similarity	NPC92730
0.8854	High Similarity	NPC76938
0.8846	High Similarity	NPC308689
0.8846	High Similarity	NPC177576
0.8835	High Similarity	NPC265211
0.8835	High Similarity	NPC474272
0.8835	High Similarity	NPC306045
0.883	High Similarity	NPC177420
0.883	High Similarity	NPC123273
0.883	High Similarity	NPC280347
0.883	High Similarity	NPC318325
0.883	High Similarity	NPC242240
0.8812	High Similarity	NPC474839
0.88	High Similarity	NPC168829
0.8776	High Similarity	NPC474073
0.8776	High Similarity	NPC225464
0.8774	High Similarity	NPC473137
0.8763	High Similarity	NPC32714
0.8737	High Similarity	NPC55561
0.8737	High Similarity	NPC300478
0.8725	High Similarity	NPC113457
0.8723	High Similarity	NPC25493
0.8723	High Similarity	NPC113460
0.8713	High Similarity	NPC261573
0.8713	High Similarity	NPC288411
0.8713	High Similarity	NPC119860
0.8713	High Similarity	NPC120693
0.8713	High Similarity	NPC8931
0.87	High Similarity	NPC101025
0.87	High Similarity	NPC471578
0.8632	High Similarity	NPC258219
0.8627	High Similarity	NPC138942
0.8617	High Similarity	NPC23167
0.8614	High Similarity	NPC135784
0.8611	High Similarity	NPC473556
0.8611	High Similarity	NPC301651
0.8602	High Similarity	NPC175313
0.8598	High Similarity	NPC12656
0.8598	High Similarity	NPC285350
0.8598	High Similarity	NPC120280
0.8586	High Similarity	NPC201967
0.8585	High Similarity	NPC228425
0.8558	High Similarity	NPC61885
0.8558	High Similarity	NPC317305
0.8558	High Similarity	NPC63698
0.8557	High Similarity	NPC271440
0.8544	High Similarity	NPC188677
0.8542	High Similarity	NPC192
0.8542	High Similarity	NPC47950
0.8532	High Similarity	NPC476266
0.8529	High Similarity	NPC30506
0.8529	High Similarity	NPC241891
0.8511	High Similarity	NPC197783
0.8505	High Similarity	NPC123175
0.8505	High Similarity	NPC176730
0.85	High Similarity	NPC130193
0.8495	Intermediate Similarity	NPC265146
0.8495	Intermediate Similarity	NPC99482
0.8469	Intermediate Similarity	NPC27323
0.8469	Intermediate Similarity	NPC316301
0.8462	Intermediate Similarity	NPC61033
0.8462	Intermediate Similarity	NPC305603
0.8454	Intermediate Similarity	NPC270547
0.8454	Intermediate Similarity	NPC304541
0.8447	Intermediate Similarity	NPC134829
0.8438	Intermediate Similarity	NPC98772
0.8431	Intermediate Similarity	NPC62351
0.8421	Intermediate Similarity	NPC184169
0.8411	Intermediate Similarity	NPC228988
0.8404	Intermediate Similarity	NPC248817
0.84	Intermediate Similarity	NPC32674
0.8396	Intermediate Similarity	NPC183700
0.8381	Intermediate Similarity	NPC75440
0.8381	Intermediate Similarity	NPC201959
0.8381	Intermediate Similarity	NPC11554
0.8378	Intermediate Similarity	NPC109371
0.8378	Intermediate Similarity	NPC470214
0.8378	Intermediate Similarity	NPC470215
0.8367	Intermediate Similarity	NPC162314
0.8367	Intermediate Similarity	NPC210497
0.8367	Intermediate Similarity	NPC3358
0.8367	Intermediate Similarity	NPC147284
0.8367	Intermediate Similarity	NPC306884
0.8367	Intermediate Similarity	NPC94139
0.8365	Intermediate Similarity	NPC271274
0.8365	Intermediate Similarity	NPC109691
0.8365	Intermediate Similarity	NPC470700
0.8365	Intermediate Similarity	NPC95178
0.8365	Intermediate Similarity	NPC118286
0.8365	Intermediate Similarity	NPC39664
0.8365	Intermediate Similarity	NPC302681
0.8365	Intermediate Similarity	NPC70843
0.8365	Intermediate Similarity	NPC39097
0.8365	Intermediate Similarity	NPC248904
0.8365	Intermediate Similarity	NPC69332
0.8365	Intermediate Similarity	NPC29989
0.8351	Intermediate Similarity	NPC312304
0.835	Intermediate Similarity	NPC471511
0.8349	Intermediate Similarity	NPC23402
0.8333	Intermediate Similarity	NPC110764
0.8333	Intermediate Similarity	NPC100340
0.8333	Intermediate Similarity	NPC261343
0.8333	Intermediate Similarity	NPC143659
0.8318	Intermediate Similarity	NPC225679
0.8318	Intermediate Similarity	NPC165770
0.8318	Intermediate Similarity	NPC4493
0.8318	Intermediate Similarity	NPC476632
0.8316	Intermediate Similarity	NPC155393
0.8304	Intermediate Similarity	NPC223451
0.8302	Intermediate Similarity	NPC88141
0.8302	Intermediate Similarity	NPC228343
0.8302	Intermediate Similarity	NPC254833
0.8298	Intermediate Similarity	NPC124436
0.8288	Intermediate Similarity	NPC86198
0.8288	Intermediate Similarity	NPC249435
0.8286	Intermediate Similarity	NPC54844
0.8286	Intermediate Similarity	NPC260952
0.8273	Intermediate Similarity	NPC137496
0.8273	Intermediate Similarity	NPC474358
0.8273	Intermediate Similarity	NPC257540
0.8273	Intermediate Similarity	NPC474387
0.8273	Intermediate Similarity	NPC154511
0.8273	Intermediate Similarity	NPC247858
0.8269	Intermediate Similarity	NPC239291
0.8269	Intermediate Similarity	NPC246056
0.8269	Intermediate Similarity	NPC219286
0.8269	Intermediate Similarity	NPC99557
0.8265	Intermediate Similarity	NPC204210
0.8265	Intermediate Similarity	NPC155908
0.8252	Intermediate Similarity	NPC68269
0.8252	Intermediate Similarity	NPC471228
0.8252	Intermediate Similarity	NPC235762
0.8241	Intermediate Similarity	NPC166995
0.8241	Intermediate Similarity	NPC43525
0.8235	Intermediate Similarity	NPC275053
0.8235	Intermediate Similarity	NPC10588
0.8235	Intermediate Similarity	NPC174911
0.8235	Intermediate Similarity	NPC248573
0.8235	Intermediate Similarity	NPC225506
0.8235	Intermediate Similarity	NPC161571
0.823	Intermediate Similarity	NPC201402
0.823	Intermediate Similarity	NPC469704
0.823	Intermediate Similarity	NPC469703
0.823	Intermediate Similarity	NPC160854
0.8229	Intermediate Similarity	NPC407
0.8229	Intermediate Similarity	NPC307235
0.8224	Intermediate Similarity	NPC296683
0.8218	Intermediate Similarity	NPC77492
0.8214	Intermediate Similarity	NPC151197
0.8214	Intermediate Similarity	NPC70084
0.8214	Intermediate Similarity	NPC182240
0.8208	Intermediate Similarity	NPC206341

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 NPC213730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	924
0.2-0.3	1272
0.3-0.4	2834
0.4-0.5	2007
0.5-0.6	1217
0.6-0.7	525
0.7-0.8	101
0.8-0.85	8
0.85-0.9	0
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9362	High Similarity	NPD2859	Approved
0.9362	High Similarity	NPD2860	Approved
0.9255	High Similarity	NPD2933	Approved
0.9255	High Similarity	NPD2934	Approved
0.9072	High Similarity	NPD3020	Approved
0.8469	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD846	Approved
0.8333	Intermediate Similarity	NPD940	Approved
0.8302	Intermediate Similarity	NPD3021	Approved
0.8302	Intermediate Similarity	NPD3022	Approved
0.8298	Intermediate Similarity	NPD111	Approved
0.8235	Intermediate Similarity	NPD1242	Phase 1
0.8142	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3091	Approved
0.8058	Intermediate Similarity	NPD3028	Approved
0.802	Intermediate Similarity	NPD1809	Phase 2
0.802	Intermediate Similarity	NPD844	Approved
0.8	Intermediate Similarity	NPD845	Approved
0.7963	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2684	Approved
0.7863	Intermediate Similarity	NPD4659	Approved
0.785	Intermediate Similarity	NPD968	Approved
0.7845	Intermediate Similarity	NPD3092	Approved
0.7838	Intermediate Similarity	NPD2228	Approved
0.7838	Intermediate Similarity	NPD2234	Approved
0.7838	Intermediate Similarity	NPD2229	Approved
0.7778	Intermediate Similarity	NPD2562	Approved
0.7778	Intermediate Similarity	NPD2561	Approved
0.7767	Intermediate Similarity	NPD288	Approved
0.7731	Intermediate Similarity	NPD3094	Phase 2
0.7731	Intermediate Similarity	NPD4103	Phase 2
0.7731	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD3095	Discontinued
0.7658	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1548	Phase 1
0.7636	Intermediate Similarity	NPD5451	Approved
0.7636	Intermediate Similarity	NPD4750	Phase 3
0.7634	Intermediate Similarity	NPD9294	Approved
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7615	Intermediate Similarity	NPD2342	Discontinued
0.7589	Intermediate Similarity	NPD7635	Approved
0.7589	Intermediate Similarity	NPD7843	Approved
0.757	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD16	Approved
0.7565	Intermediate Similarity	NPD856	Approved
0.7563	Intermediate Similarity	NPD6583	Phase 3
0.7563	Intermediate Similarity	NPD6582	Phase 2
0.7542	Intermediate Similarity	NPD1610	Phase 2
0.7542	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5846	Approved
0.7521	Intermediate Similarity	NPD6516	Phase 2
0.75	Intermediate Similarity	NPD6407	Approved
0.75	Intermediate Similarity	NPD9610	Approved
0.75	Intermediate Similarity	NPD5303	Approved
0.75	Intermediate Similarity	NPD6405	Approved
0.75	Intermediate Similarity	NPD9608	Approved
0.75	Intermediate Similarity	NPD5304	Approved
0.7477	Intermediate Similarity	NPD1792	Phase 2
0.7459	Intermediate Similarity	NPD2861	Phase 2
0.7458	Intermediate Similarity	NPD3421	Phase 3
0.7455	Intermediate Similarity	NPD290	Approved
0.7436	Intermediate Similarity	NPD4093	Discontinued
0.7417	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD317	Approved
0.7414	Intermediate Similarity	NPD318	Approved
0.7398	Intermediate Similarity	NPD4908	Phase 1
0.7391	Intermediate Similarity	NPD7157	Approved
0.7377	Intermediate Similarity	NPD6584	Phase 3
0.7373	Intermediate Similarity	NPD2286	Discontinued
0.7373	Intermediate Similarity	NPD4589	Approved
0.7373	Intermediate Similarity	NPD3019	Approved
0.7373	Intermediate Similarity	NPD2932	Approved
0.7373	Intermediate Similarity	NPD4059	Approved
0.7368	Intermediate Similarity	NPD5283	Phase 1
0.7364	Intermediate Similarity	NPD1444	Approved
0.7364	Intermediate Similarity	NPD1445	Approved
0.7358	Intermediate Similarity	NPD9273	Approved
0.7345	Intermediate Similarity	NPD228	Approved
0.7339	Intermediate Similarity	NPD1237	Approved
0.7317	Intermediate Similarity	NPD5736	Approved
0.7312	Intermediate Similarity	NPD9087	Approved
0.7311	Intermediate Similarity	NPD3847	Discontinued
0.7304	Intermediate Similarity	NPD9614	Approved
0.7304	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD9618	Approved
0.7297	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1129	Approved
0.7295	Intermediate Similarity	NPD1131	Approved
0.7295	Intermediate Similarity	NPD1133	Approved
0.7295	Intermediate Similarity	NPD1134	Approved
0.7295	Intermediate Similarity	NPD1135	Approved
0.7281	Intermediate Similarity	NPD821	Approved
0.7281	Intermediate Similarity	NPD5535	Approved
0.728	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3554	Approved
0.7266	Intermediate Similarity	NPD3552	Approved
0.7266	Intermediate Similarity	NPD3553	Approved
0.7266	Intermediate Similarity	NPD3555	Approved
0.7241	Intermediate Similarity	NPD6671	Approved
0.7227	Intermediate Similarity	NPD2668	Approved
0.7227	Intermediate Similarity	NPD9384	Approved
0.7227	Intermediate Similarity	NPD9381	Approved
0.7227	Intermediate Similarity	NPD2667	Approved
0.7217	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1894	Discontinued
0.719	Intermediate Similarity	NPD2231	Phase 2
0.719	Intermediate Similarity	NPD2235	Phase 2
0.7188	Intermediate Similarity	NPD9088	Approved
0.7188	Intermediate Similarity	NPD2568	Approved
0.7179	Intermediate Similarity	NPD3596	Phase 2
0.7165	Intermediate Similarity	NPD3062	Approved
0.7165	Intermediate Similarity	NPD3059	Approved
0.7165	Intermediate Similarity	NPD1613	Approved
0.7165	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3061	Approved
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD3685	Discontinued
0.713	Intermediate Similarity	NPD9379	Approved
0.713	Intermediate Similarity	NPD9377	Approved
0.7119	Intermediate Similarity	NPD9615	Approved
0.7119	Intermediate Similarity	NPD9616	Approved
0.7119	Intermediate Similarity	NPD9613	Approved
0.7105	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD256	Approved
0.7094	Intermediate Similarity	NPD255	Approved
0.7087	Intermediate Similarity	NPD6663	Approved
0.7083	Intermediate Similarity	NPD1751	Approved
0.7073	Intermediate Similarity	NPD5311	Approved
0.7073	Intermediate Similarity	NPD5310	Approved
0.7071	Intermediate Similarity	NPD9089	Approved
0.7059	Intermediate Similarity	NPD316	Approved
0.7059	Intermediate Similarity	NPD6580	Approved
0.7059	Intermediate Similarity	NPD6581	Approved
0.7059	Intermediate Similarity	NPD7330	Discontinued
0.7054	Intermediate Similarity	NPD3054	Approved
0.7054	Intermediate Similarity	NPD5314	Approved
0.7054	Intermediate Similarity	NPD3134	Approved
0.7054	Intermediate Similarity	NPD3052	Approved
0.7037	Intermediate Similarity	NPD9495	Approved
0.7034	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3620	Phase 2
0.7031	Intermediate Similarity	NPD2238	Phase 2
0.7031	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4060	Phase 1
0.7016	Intermediate Similarity	NPD3055	Approved
0.7016	Intermediate Similarity	NPD1164	Approved
0.7016	Intermediate Similarity	NPD3053	Approved
0.7008	Intermediate Similarity	NPD6798	Discontinued
0.7008	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD4536	Approved
0.7	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4538	Approved
0.6992	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9622	Approved
0.6991	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9093	Approved
0.697	Remote Similarity	NPD7266	Discontinued
0.6967	Remote Similarity	NPD1535	Discovery
0.6967	Remote Similarity	NPD1091	Approved
0.6964	Remote Similarity	NPD5048	Discontinued
0.696	Remote Similarity	NPD3691	Phase 2
0.696	Remote Similarity	NPD3690	Phase 2
0.696	Remote Similarity	NPD7451	Discontinued
0.6953	Remote Similarity	NPD6233	Phase 2
0.6949	Remote Similarity	NPD2557	Approved
0.6947	Remote Similarity	NPD7742	Approved
0.6947	Remote Similarity	NPD7743	Approved
0.6947	Remote Similarity	NPD5588	Approved
0.6947	Remote Similarity	NPD5960	Phase 3
0.6942	Remote Similarity	NPD4626	Approved
0.694	Remote Similarity	NPD3400	Discontinued
0.6937	Remote Similarity	NPD4658	Approved
0.6937	Remote Similarity	NPD9500	Approved
0.6937	Remote Similarity	NPD4656	Approved
0.6935	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3136	Phase 2
0.6929	Remote Similarity	NPD6179	Discontinued
0.6917	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9545	Approved
0.6911	Remote Similarity	NPD2230	Approved
0.6911	Remote Similarity	NPD1481	Phase 2
0.6911	Remote Similarity	NPD2232	Approved
0.6911	Remote Similarity	NPD2233	Approved
0.6909	Remote Similarity	NPD2553	Approved
0.6909	Remote Similarity	NPD2552	Approved
0.6909	Remote Similarity	NPD2555	Approved
0.6909	Remote Similarity	NPD2549	Approved
0.6909	Remote Similarity	NPD2550	Approved
0.6909	Remote Similarity	NPD2558	Approved
0.6899	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4140	Approved
0.6891	Remote Similarity	NPD9568	Approved
0.6881	Remote Similarity	NPD9609	Approved
0.6881	Remote Similarity	NPD9611	Approved
0.6881	Remote Similarity	NPD9612	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