NPASS Compound

Structure

CID141607 OpenBabel06191715502D 21 22 0 0 1 0 0 0 0 0999 V2000 -6.0622 3.5000 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 -5.1962 3.0000 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 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 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 -6.0622 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 0.5000 0.0000 C 0 0 2 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 -4.3301 1.5000 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 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 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 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 18 20 1 1 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.16
Volume:	319.193
LogP:	3.064
LogD:	3.205
LogS:	-4.096
# Rotatable Bonds:	8
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	2.225
Fsp3:	0.316
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:	-4.741
MDCK Permeability:	1.937475462909788e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	95.13542938232422%
Volume Distribution (VD):	0.796
Pgp-substrate:	1.1750857830047607%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.434
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.088
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	10.585
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.742
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.641
Carcinogencity:	0.363
Eye Corrosion:	0.013
Eye Irritation:	0.922
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC141607

Natural Product ID:	NPC141607
*Common Name:**	(R)-5-Hydroxy-1,7-Diphenylheptan-3-One
IUPAC Name:	(5R)-5-hydroxy-1,7-diphenylheptan-3-one
Synonyms:
Standard InCHIKey:	CCNKTMMNRPJQHV-GOSISDBHSA-N
Standard InCHI:	InChI=1S/C19H22O2/c20-18(13-11-16-7-3-1-4-8-16)15-19(21)14-12-17-9-5-2-6-10-17/h1-10,18,20H,11-15H2/t18-/m1/s1
SMILES:	c1ccc(cc1)CC[C@H](CC(=O)CCc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL594066
PubChem CID:	46213118
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
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
IC50	3
Others	15

Activity Type	# Activity
Cell Line	1
Individual Protein	6
NON-MOLECULAR	6
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	48000.0	nM	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.3	%	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.5	%	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.4	%	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.4	%	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	2.1	%	PMID[529328]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	100000.0	nM	PMID[529328]
NPT2	Others	Unspecified		Inhibition	=	-3.3	%	PMID[529328]
NPT2	Others	Unspecified		Inhibition	=	6.8	%	PMID[529328]
NPT2	Others	Unspecified		Inhibition	=	10.6	%	PMID[529328]
NPT2	Others	Unspecified		Inhibition	=	33.0	%	PMID[529328]
NPT2	Others	Unspecified		Inhibition	=	67.8	%	PMID[529328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.0	%	PMID[529328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.7	%	PMID[529328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-4.7	%	PMID[529328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-7.6	%	PMID[529328]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[529328]

☑ 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 NPC141607 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	191
0.1-0.2	858
0.2-0.3	2662
0.3-0.4	10441
0.4-0.5	16020
0.5-0.6	10496
0.6-0.7	1739
0.7-0.8	258
0.8-0.85	23
0.85-0.9	5
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC187725
0.9659	High Similarity	NPC206764
0.931	High Similarity	NPC231591
0.8817	High Similarity	NPC289201
0.8721	High Similarity	NPC73637
0.8721	High Similarity	NPC121478
0.8706	High Similarity	NPC164449
0.8706	High Similarity	NPC184030
0.8485	Intermediate Similarity	NPC25385
0.8485	Intermediate Similarity	NPC193640
0.8485	Intermediate Similarity	NPC475905
0.8427	Intermediate Similarity	NPC99482
0.8409	Intermediate Similarity	NPC44830
0.8372	Intermediate Similarity	NPC272260
0.8353	Intermediate Similarity	NPC9796
0.8352	Intermediate Similarity	NPC477693
0.8352	Intermediate Similarity	NPC477704
0.8351	Intermediate Similarity	NPC158623
0.8333	Intermediate Similarity	NPC329387
0.8333	Intermediate Similarity	NPC252544
0.8333	Intermediate Similarity	NPC321252
0.8333	Intermediate Similarity	NPC317280
0.8295	Intermediate Similarity	NPC283012
0.8295	Intermediate Similarity	NPC475199
0.8252	Intermediate Similarity	NPC177576
0.82	Intermediate Similarity	NPC474307
0.8105	Intermediate Similarity	NPC34243
0.81	Intermediate Similarity	NPC19136
0.81	Intermediate Similarity	NPC249067
0.8085	Intermediate Similarity	NPC317645
0.8068	Intermediate Similarity	NPC127343
0.8065	Intermediate Similarity	NPC9822
0.8061	Intermediate Similarity	NPC476042
0.8061	Intermediate Similarity	NPC54647
0.8041	Intermediate Similarity	NPC477767
0.8022	Intermediate Similarity	NPC95965
0.8022	Intermediate Similarity	NPC123476
0.8022	Intermediate Similarity	NPC475710
0.802	Intermediate Similarity	NPC471186
0.802	Intermediate Similarity	NPC321670
0.8019	Intermediate Similarity	NPC285350
0.7961	Intermediate Similarity	NPC317305
0.7959	Intermediate Similarity	NPC271475
0.7955	Intermediate Similarity	NPC139901
0.7955	Intermediate Similarity	NPC151405
0.7865	Intermediate Similarity	NPC477703
0.7864	Intermediate Similarity	NPC20485
0.7802	Intermediate Similarity	NPC285773
0.7788	Intermediate Similarity	NPC475282
0.7778	Intermediate Similarity	NPC23402
0.7765	Intermediate Similarity	NPC208302
0.7745	Intermediate Similarity	NPC120693
0.7745	Intermediate Similarity	NPC261573
0.7745	Intermediate Similarity	NPC8931
0.7736	Intermediate Similarity	NPC471189
0.7736	Intermediate Similarity	NPC471188
0.7727	Intermediate Similarity	NPC249435
0.7685	Intermediate Similarity	NPC215419
0.7677	Intermediate Similarity	NPC103048
0.7667	Intermediate Similarity	NPC95868
0.766	Intermediate Similarity	NPC69057
0.766	Intermediate Similarity	NPC322387
0.7658	Intermediate Similarity	NPC182240
0.7653	Intermediate Similarity	NPC172925
0.7647	Intermediate Similarity	NPC329556
0.7642	Intermediate Similarity	NPC265513
0.7624	Intermediate Similarity	NPC94487
0.7624	Intermediate Similarity	NPC225079
0.7609	Intermediate Similarity	NPC273758
0.7604	Intermediate Similarity	NPC70940
0.7604	Intermediate Similarity	NPC86670
0.7604	Intermediate Similarity	NPC274455
0.76	Intermediate Similarity	NPC175852
0.76	Intermediate Similarity	NPC160548
0.76	Intermediate Similarity	NPC210529
0.7596	Intermediate Similarity	NPC188677
0.7596	Intermediate Similarity	NPC94751
0.7596	Intermediate Similarity	NPC142326
0.7589	Intermediate Similarity	NPC34634
0.7589	Intermediate Similarity	NPC265454
0.7586	Intermediate Similarity	NPC108218
0.7582	Intermediate Similarity	NPC273033
0.7582	Intermediate Similarity	NPC12936
0.7579	Intermediate Similarity	NPC329064
0.7576	Intermediate Similarity	NPC12695
0.7558	Intermediate Similarity	NPC74458
0.7549	Intermediate Similarity	NPC475978
0.7549	Intermediate Similarity	NPC474820
0.7528	Intermediate Similarity	NPC179726
0.7527	Intermediate Similarity	NPC304538
0.7526	Intermediate Similarity	NPC86987
0.7524	Intermediate Similarity	NPC211439
0.7524	Intermediate Similarity	NPC470007
0.75	Intermediate Similarity	NPC470253
0.7477	Intermediate Similarity	NPC471553
0.7476	Intermediate Similarity	NPC247976
0.7474	Intermediate Similarity	NPC194326
0.7473	Intermediate Similarity	NPC71664
0.7471	Intermediate Similarity	NPC285679
0.7471	Intermediate Similarity	NPC271437
0.7455	Intermediate Similarity	NPC9274
0.7455	Intermediate Similarity	NPC471616
0.7455	Intermediate Similarity	NPC188010
0.7451	Intermediate Similarity	NPC136810
0.7451	Intermediate Similarity	NPC133809
0.7451	Intermediate Similarity	NPC128248
0.7447	Intermediate Similarity	NPC294134
0.7444	Intermediate Similarity	NPC103488
0.7444	Intermediate Similarity	NPC224544
0.7429	Intermediate Similarity	NPC69332
0.7429	Intermediate Similarity	NPC29989
0.7429	Intermediate Similarity	NPC329705
0.7429	Intermediate Similarity	NPC70843
0.7429	Intermediate Similarity	NPC95178
0.7429	Intermediate Similarity	NPC474111
0.7426	Intermediate Similarity	NPC145052
0.7426	Intermediate Similarity	NPC476120
0.7423	Intermediate Similarity	NPC84288
0.7419	Intermediate Similarity	NPC288903
0.7419	Intermediate Similarity	NPC477770
0.7407	Intermediate Similarity	NPC218855
0.7404	Intermediate Similarity	NPC329282
0.7391	Intermediate Similarity	NPC86900
0.7391	Intermediate Similarity	NPC117180
0.7386	Intermediate Similarity	NPC208075
0.7383	Intermediate Similarity	NPC88141
0.7368	Intermediate Similarity	NPC98305
0.7353	Intermediate Similarity	NPC78119
0.7353	Intermediate Similarity	NPC216468
0.7353	Intermediate Similarity	NPC51333
0.7353	Intermediate Similarity	NPC132078
0.7347	Intermediate Similarity	NPC476484
0.7347	Intermediate Similarity	NPC110704
0.7339	Intermediate Similarity	NPC206414
0.7339	Intermediate Similarity	NPC306977
0.7339	Intermediate Similarity	NPC242957
0.7339	Intermediate Similarity	NPC287055
0.7339	Intermediate Similarity	NPC471481
0.7333	Intermediate Similarity	NPC298023
0.7333	Intermediate Similarity	NPC134120
0.7327	Intermediate Similarity	NPC226041
0.7327	Intermediate Similarity	NPC278228
0.7327	Intermediate Similarity	NPC270654
0.7312	Intermediate Similarity	NPC99394
0.7312	Intermediate Similarity	NPC323103
0.7312	Intermediate Similarity	NPC103326
0.7312	Intermediate Similarity	NPC329319
0.7312	Intermediate Similarity	NPC87299
0.7308	Intermediate Similarity	NPC160382
0.7303	Intermediate Similarity	NPC189371
0.729	Intermediate Similarity	NPC40178
0.7283	Intermediate Similarity	NPC17408
0.7283	Intermediate Similarity	NPC157055
0.7283	Intermediate Similarity	NPC285716
0.7282	Intermediate Similarity	NPC294741
0.7282	Intermediate Similarity	NPC469481
0.7282	Intermediate Similarity	NPC213730
0.7282	Intermediate Similarity	NPC264728
0.7281	Intermediate Similarity	NPC473136
0.7273	Intermediate Similarity	NPC234637
0.7273	Intermediate Similarity	NPC77273
0.7273	Intermediate Similarity	NPC172525
0.7273	Intermediate Similarity	NPC196673
0.7273	Intermediate Similarity	NPC130591
0.7273	Intermediate Similarity	NPC294458
0.7265	Intermediate Similarity	NPC231767
0.7264	Intermediate Similarity	NPC85560
0.7264	Intermediate Similarity	NPC100767
0.7264	Intermediate Similarity	NPC83409
0.7264	Intermediate Similarity	NPC185763
0.7264	Intermediate Similarity	NPC244933
0.7257	Intermediate Similarity	NPC318173
0.7253	Intermediate Similarity	NPC137847
0.7253	Intermediate Similarity	NPC76455
0.7248	Intermediate Similarity	NPC158282
0.7234	Intermediate Similarity	NPC270507
0.7212	Intermediate Similarity	NPC91461
0.7212	Intermediate Similarity	NPC7686
0.7212	Intermediate Similarity	NPC40258
0.7212	Intermediate Similarity	NPC474112
0.7204	Intermediate Similarity	NPC73978
0.7203	Intermediate Similarity	NPC127975
0.7196	Intermediate Similarity	NPC112903
0.7196	Intermediate Similarity	NPC47536
0.7193	Intermediate Similarity	NPC476645
0.7184	Intermediate Similarity	NPC474308
0.7184	Intermediate Similarity	NPC221825
0.7182	Intermediate Similarity	NPC477475
0.7182	Intermediate Similarity	NPC477476
0.7182	Intermediate Similarity	NPC286222
0.7174	Intermediate Similarity	NPC300205
0.7174	Intermediate Similarity	NPC469894
0.7172	Intermediate Similarity	NPC220596
0.7158	Intermediate Similarity	NPC95429
0.7157	Intermediate Similarity	NPC156021
0.7157	Intermediate Similarity	NPC324602
0.7157	Intermediate Similarity	NPC240042
0.7155	Intermediate Similarity	NPC31936
0.7143	Intermediate Similarity	NPC199567
0.7143	Intermediate Similarity	NPC298115

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 NPC141607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	810
0.2-0.3	1268
0.3-0.4	3035
0.4-0.5	2444
0.5-0.6	1110
0.6-0.7	274
0.7-0.8	41
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.82	Intermediate Similarity	NPD5048	Discontinued
0.8105	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD1237	Approved
0.8043	Intermediate Similarity	NPD4793	Discontinued
0.7978	Intermediate Similarity	NPD226	Approved
0.7895	Intermediate Similarity	NPD1239	Approved
0.7879	Intermediate Similarity	NPD2066	Phase 3
0.7872	Intermediate Similarity	NPD5347	Phase 2
0.7872	Intermediate Similarity	NPD5346	Phase 2
0.7802	Intermediate Similarity	NPD9491	Approved
0.7755	Intermediate Similarity	NPD1989	Approved
0.7755	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD1932	Approved
0.77	Intermediate Similarity	NPD7798	Approved
0.7684	Intermediate Similarity	NPD800	Approved
0.7667	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD1693	Approved
0.7653	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1930	Approved
0.7647	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1929	Approved
0.7642	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD227	Approved
0.764	Intermediate Similarity	NPD225	Approved
0.7604	Intermediate Similarity	NPD1089	Approved
0.7604	Intermediate Similarity	NPD3673	Approved
0.7604	Intermediate Similarity	NPD1090	Approved
0.7604	Intermediate Similarity	NPD3672	Approved
0.7604	Intermediate Similarity	NPD1086	Approved
0.76	Intermediate Similarity	NPD9495	Approved
0.7582	Intermediate Similarity	NPD942	Approved
0.75	Intermediate Similarity	NPD1564	Approved
0.75	Intermediate Similarity	NPD1565	Approved
0.75	Intermediate Similarity	NPD1566	Phase 3
0.7476	Intermediate Similarity	NPD5765	Approved
0.7476	Intermediate Similarity	NPD6647	Phase 2
0.7449	Intermediate Similarity	NPD1088	Approved
0.7429	Intermediate Similarity	NPD467	Phase 1
0.7404	Intermediate Similarity	NPD5909	Discontinued
0.7364	Intermediate Similarity	NPD2629	Approved
0.7363	Intermediate Similarity	NPD9490	Approved
0.7308	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1087	Approved
0.729	Intermediate Similarity	NPD2329	Discontinued
0.7282	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6010	Discontinued
0.7264	Intermediate Similarity	NPD6685	Approved
0.72	Intermediate Similarity	NPD1563	Approved
0.7184	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3317	Approved
0.7117	Intermediate Similarity	NPD2652	Approved
0.7117	Intermediate Similarity	NPD2650	Approved
0.7054	Intermediate Similarity	NPD1711	Phase 2
0.7048	Intermediate Similarity	NPD4719	Phase 2
0.7034	Intermediate Similarity	NPD5159	Phase 2
0.7034	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5157	Phase 1
0.703	Intermediate Similarity	NPD1066	Discontinued
0.7027	Intermediate Similarity	NPD7094	Approved
0.7027	Intermediate Similarity	NPD6858	Approved
0.7009	Intermediate Similarity	NPD3132	Approved
0.7009	Intermediate Similarity	NPD2610	Approved
0.7009	Intermediate Similarity	NPD4215	Approved
0.7009	Intermediate Similarity	NPD2608	Approved
0.7009	Intermediate Similarity	NPD4218	Approved
0.7009	Intermediate Similarity	NPD2611	Approved
0.7009	Intermediate Similarity	NPD4216	Approved
0.7009	Intermediate Similarity	NPD4217	Approved
0.7009	Intermediate Similarity	NPD3131	Approved
0.7009	Intermediate Similarity	NPD2609	Approved
0.7009	Intermediate Similarity	NPD2612	Approved
0.7	Intermediate Similarity	NPD7609	Phase 3
0.6981	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4094	Approved
0.6957	Remote Similarity	NPD9294	Approved
0.6937	Remote Similarity	NPD6912	Phase 3
0.6931	Remote Similarity	NPD1508	Approved
0.6931	Remote Similarity	NPD7631	Approved
0.6923	Remote Similarity	NPD253	Approved
0.6893	Remote Similarity	NPD2859	Approved
0.6893	Remote Similarity	NPD2860	Approved
0.6863	Remote Similarity	NPD3718	Approved
0.6863	Remote Similarity	NPD3719	Approved
0.6863	Remote Similarity	NPD1202	Approved
0.6857	Remote Similarity	NPD1238	Approved
0.6847	Remote Similarity	NPD3644	Approved
0.6847	Remote Similarity	NPD3643	Approved
0.6847	Remote Similarity	NPD3642	Approved
0.6827	Remote Similarity	NPD9566	Approved
0.6827	Remote Similarity	NPD4657	Approved
0.6827	Remote Similarity	NPD4655	Approved
0.6827	Remote Similarity	NPD3495	Discontinued
0.6818	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2934	Approved
0.6796	Remote Similarity	NPD2933	Approved
0.6796	Remote Similarity	NPD4814	Discontinued
0.6783	Remote Similarity	NPD4574	Approved
0.6783	Remote Similarity	NPD4576	Approved
0.678	Remote Similarity	NPD4106	Approved
0.678	Remote Similarity	NPD4135	Approved
0.678	Remote Similarity	NPD4136	Approved
0.6768	Remote Similarity	NPD650	Approved
0.6762	Remote Similarity	NPD5926	Approved
0.6757	Remote Similarity	NPD2067	Discontinued
0.6757	Remote Similarity	NPD1317	Discontinued
0.6757	Remote Similarity	NPD5278	Discontinued
0.6757	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5951	Approved
0.6752	Remote Similarity	NPD5981	Approved
0.6733	Remote Similarity	NPD9256	Approved
0.6733	Remote Similarity	NPD9258	Approved
0.6731	Remote Similarity	NPD1843	Approved
0.6727	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7610	Discontinued
0.6724	Remote Similarity	NPD6065	Approved
0.6721	Remote Similarity	NPD6085	Phase 2
0.6721	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3971	Phase 1
0.6698	Remote Similarity	NPD3020	Approved
0.6697	Remote Similarity	NPD1018	Approved
0.6696	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5306	Approved
0.6695	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD1875	Phase 1
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD3598	Phase 3
0.6639	Remote Similarity	NPD4879	Approved
0.6638	Remote Similarity	NPD5162	Approved
0.6636	Remote Similarity	NPD5704	Approved
0.6636	Remote Similarity	NPD5706	Approved
0.6636	Remote Similarity	NPD5705	Approved
0.6613	Remote Similarity	NPD2613	Approved
0.661	Remote Similarity	NPD4105	Approved
0.661	Remote Similarity	NPD4102	Approved
0.6585	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4806	Approved
0.6583	Remote Similarity	NPD4807	Approved
0.6583	Remote Similarity	NPD1201	Approved
0.6583	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6027	Approved
0.6574	Remote Similarity	NPD6024	Approved
0.6555	Remote Similarity	NPD2345	Approved
0.6555	Remote Similarity	NPD3019	Approved
0.6555	Remote Similarity	NPD2932	Approved
0.6552	Remote Similarity	NPD675	Discontinued
0.6549	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1101	Approved
0.6535	Remote Similarity	NPD531	Approved
0.6532	Remote Similarity	NPD5204	Approved
0.6529	Remote Similarity	NPD4878	Approved
0.6525	Remote Similarity	NPD4479	Discontinued
0.6522	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9259	Approved
0.65	Remote Similarity	NPD9257	Approved
0.6496	Remote Similarity	NPD3797	Approved
0.6481	Remote Similarity	NPD2555	Approved
0.6481	Remote Similarity	NPD2558	Approved
0.6481	Remote Similarity	NPD2550	Approved
0.6481	Remote Similarity	NPD2552	Approved
0.6481	Remote Similarity	NPD2549	Approved
0.6481	Remote Similarity	NPD2553	Approved
0.648	Remote Similarity	NPD4620	Approved
0.648	Remote Similarity	NPD4617	Approved
0.648	Remote Similarity	NPD5201	Approved
0.648	Remote Similarity	NPD5203	Approved
0.6476	Remote Similarity	NPD3772	Phase 3
0.6471	Remote Similarity	NPD6994	Approved
0.6471	Remote Similarity	NPD6993	Approved
0.6466	Remote Similarity	NPD1246	Approved
0.646	Remote Similarity	NPD4234	Approved
0.646	Remote Similarity	NPD1752	Approved
0.646	Remote Similarity	NPD1756	Approved
0.646	Remote Similarity	NPD4233	Approved
0.6457	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3089	Approved
0.6457	Remote Similarity	NPD2566	Approved
0.6457	Remote Similarity	NPD4746	Phase 3
0.6457	Remote Similarity	NPD4745	Approved
0.6457	Remote Similarity	NPD2574	Discontinued
0.6457	Remote Similarity	NPD3087	Approved
0.6457	Remote Similarity	NPD3616	Approved
0.6457	Remote Similarity	NPD2571	Approved
0.6457	Remote Similarity	NPD7715	Approved
0.6457	Remote Similarity	NPD3614	Approved
0.6457	Remote Similarity	NPD7714	Approved
0.6457	Remote Similarity	NPD2573	Approved
0.6457	Remote Similarity	NPD3090	Approved
0.6457	Remote Similarity	NPD3615	Approved
0.6457	Remote Similarity	NPD2570	Approved
0.6457	Remote Similarity	NPD3088	Approved
0.6452	Remote Similarity	NPD2798	Approved
0.6436	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD2607	Approved
0.6429	Remote Similarity	NPD7008	Discontinued
0.6422	Remote Similarity	NPD4188	Approved
0.6422	Remote Similarity	NPD4189	Approved
0.6417	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4198	Discontinued
0.6406	Remote Similarity	NPD7966	Clinical (unspecified phase)

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