NPASS Compound

Structure

NPC99482 OpenBabel07101719512D 21 22 0 0 1 0 0 0 0 0999 V2000 -8.6603 1.0000 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -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 1.7321 -0.0000 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 -7.7942 -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 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 -6.9282 0.0000 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 -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 1 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 2 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 6 0 0 0 19 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	282.16
Volume:	319.193
LogP:	3.254
LogD:	3.635
LogS:	-4.051
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.816
Synthetic Accessibility Score:	2.685
Fsp3:	0.263
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:	-4.812
MDCK Permeability:	1.5194349543889984e-05
Pgp-inhibitor:	0.314
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	96.2288589477539%
Volume Distribution (VD):	0.81
Pgp-substrate:	1.7761398553848267%

ADMET: Metabolism

CYP1A2-inhibitor:	0.923
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.775
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.46
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	11.988
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.362
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.941
Carcinogencity:	0.684
Eye Corrosion:	0.326
Eye Irritation:	0.975
Respiratory Toxicity:	0.794

Download Data

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

Natural Product: NPC99482

Natural Product ID:	NPC99482
*Common Name:**	(E,3S,5S)-1,7-Diphenylhept-1-Ene-3,5-Diol
IUPAC Name:	(E,3S,5S)-1,7-diphenylhept-1-ene-3,5-diol
Synonyms:
Standard InCHIKey:	YSRHCYXKOMRFPK-SHVSIGCLSA-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/h1-11,13,18-21H,12,14-15H2/b13-11+/t18-,19+/m1/s1
SMILES:	O[C@H](C[C@@H](/C=C/c1ccccc1)O)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL579181
PubChem CID:	45483934
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
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	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
MIC	1
Others	11

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1602	Individual Protein	Neuraminidase	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	29750.0	nM	PMID[497826]
NPT2	Others	Unspecified		RFU	=	16515.3	n.a.	PMID[497827]
NPT2	Others	Unspecified		FICI	=	0.75	n.a.	PMID[497827]
NPT2	Others	Unspecified		FICI	=	0.25	n.a.	PMID[497827]
NPT2	Others	Unspecified		Ratio	=	4.0	n.a.	PMID[497827]
NPT2	Others	Unspecified		Ratio	=	2.0	n.a.	PMID[497827]
NPT2	Others	Unspecified		Ratio	=	8.0	n.a.	PMID[497827]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>=	128.0	ug.mL-1	PMID[497827]
NPT2	Others	Unspecified		RFU	=	0.746	n.a.	PMID[497827]
NPT2	Others	Unspecified		FC	=	4.0	n.a.	PMID[497827]

☑ 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 NPC99482 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	182
0.1-0.2	1087
0.2-0.3	3492
0.3-0.4	12891
0.4-0.5	14933
0.5-0.6	7894
0.6-0.7	1881
0.7-0.8	298
0.8-0.85	26
0.85-0.9	6
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.962	High Similarity	NPC283012
0.962	High Similarity	NPC475199
0.962	High Similarity	NPC73637
0.962	High Similarity	NPC121478
0.9367	High Similarity	NPC184030
0.9367	High Similarity	NPC164449
0.8764	High Similarity	NPC206764
0.869	High Similarity	NPC304538
0.8554	High Similarity	NPC117180
0.8495	Intermediate Similarity	NPC213730
0.8452	Intermediate Similarity	NPC99394
0.8452	Intermediate Similarity	NPC329319
0.8452	Intermediate Similarity	NPC103326
0.8452	Intermediate Similarity	NPC87299
0.8427	Intermediate Similarity	NPC187725
0.8427	Intermediate Similarity	NPC141607
0.8404	Intermediate Similarity	NPC7686
0.8404	Intermediate Similarity	NPC40258
0.8404	Intermediate Similarity	NPC91461
0.8387	Intermediate Similarity	NPC51333
0.8387	Intermediate Similarity	NPC132078
0.8387	Intermediate Similarity	NPC216468
0.8387	Intermediate Similarity	NPC78119
0.837	Intermediate Similarity	NPC289201
0.8354	Intermediate Similarity	NPC208302
0.8313	Intermediate Similarity	NPC469894
0.8298	Intermediate Similarity	NPC294741
0.8202	Intermediate Similarity	NPC1793
0.8202	Intermediate Similarity	NPC199567
0.8161	Intermediate Similarity	NPC475710
0.8148	Intermediate Similarity	NPC108218
0.8144	Intermediate Similarity	NPC233396
0.8144	Intermediate Similarity	NPC154899
0.8072	Intermediate Similarity	NPC66655
0.8065	Intermediate Similarity	NPC21959
0.8061	Intermediate Similarity	NPC92623
0.8061	Intermediate Similarity	NPC135464
0.8046	Intermediate Similarity	NPC95429
0.7976	Intermediate Similarity	NPC224544
0.7975	Intermediate Similarity	NPC239931
0.7975	Intermediate Similarity	NPC82770
0.7975	Intermediate Similarity	NPC78954
0.7957	Intermediate Similarity	NPC151715
0.7935	Intermediate Similarity	NPC128645
0.7931	Intermediate Similarity	NPC172984
0.7931	Intermediate Similarity	NPC477770
0.7907	Intermediate Similarity	NPC133050
0.7895	Intermediate Similarity	NPC329387
0.7895	Intermediate Similarity	NPC317280
0.7872	Intermediate Similarity	NPC26244
0.7865	Intermediate Similarity	NPC93843
0.7865	Intermediate Similarity	NPC474211
0.7857	Intermediate Similarity	NPC323810
0.7831	Intermediate Similarity	NPC189371
0.7802	Intermediate Similarity	NPC231591
0.7789	Intermediate Similarity	NPC473388
0.7778	Intermediate Similarity	NPC211237
0.7766	Intermediate Similarity	NPC76938
0.7755	Intermediate Similarity	NPC19856
0.7753	Intermediate Similarity	NPC474354
0.7745	Intermediate Similarity	NPC63345
0.7745	Intermediate Similarity	NPC475018
0.7742	Intermediate Similarity	NPC45040
0.7732	Intermediate Similarity	NPC469481
0.7732	Intermediate Similarity	NPC266343
0.7723	Intermediate Similarity	NPC262365
0.7708	Intermediate Similarity	NPC474073
0.7684	Intermediate Similarity	NPC32714
0.7677	Intermediate Similarity	NPC249067
0.767	Intermediate Similarity	NPC179002
0.767	Intermediate Similarity	NPC257430
0.767	Intermediate Similarity	NPC187583
0.767	Intermediate Similarity	NPC234376
0.766	Intermediate Similarity	NPC138117
0.766	Intermediate Similarity	NPC325292
0.7647	Intermediate Similarity	NPC474272
0.7647	Intermediate Similarity	NPC65855
0.7647	Intermediate Similarity	NPC55617
0.7647	Intermediate Similarity	NPC292758
0.7647	Intermediate Similarity	NPC62258
0.764	Intermediate Similarity	NPC168855
0.7634	Intermediate Similarity	NPC300017
0.7634	Intermediate Similarity	NPC79917
0.7634	Intermediate Similarity	NPC220596
0.7624	Intermediate Similarity	NPC472980
0.7624	Intermediate Similarity	NPC472979
0.7624	Intermediate Similarity	NPC27252
0.7604	Intermediate Similarity	NPC324602
0.7604	Intermediate Similarity	NPC292730
0.7604	Intermediate Similarity	NPC82664
0.7604	Intermediate Similarity	NPC216520
0.7604	Intermediate Similarity	NPC132271
0.76	Intermediate Similarity	NPC243601
0.76	Intermediate Similarity	NPC471133
0.7596	Intermediate Similarity	NPC42911
0.7596	Intermediate Similarity	NPC153795
0.7596	Intermediate Similarity	NPC290353
0.7596	Intermediate Similarity	NPC265002
0.7586	Intermediate Similarity	NPC328178
0.7579	Intermediate Similarity	NPC128062
0.7573	Intermediate Similarity	NPC44732
0.7573	Intermediate Similarity	NPC252544
0.7573	Intermediate Similarity	NPC147634
0.7573	Intermediate Similarity	NPC79793
0.7573	Intermediate Similarity	NPC120982
0.7573	Intermediate Similarity	NPC174096
0.7573	Intermediate Similarity	NPC321252
0.7573	Intermediate Similarity	NPC226401
0.7556	Intermediate Similarity	NPC123476
0.7553	Intermediate Similarity	NPC314690
0.7549	Intermediate Similarity	NPC64642
0.7549	Intermediate Similarity	NPC472982
0.7549	Intermediate Similarity	NPC149455
0.7528	Intermediate Similarity	NPC44830
0.7527	Intermediate Similarity	NPC213156
0.7527	Intermediate Similarity	NPC240108
0.7525	Intermediate Similarity	NPC136962
0.7525	Intermediate Similarity	NPC477251
0.75	Intermediate Similarity	NPC242913
0.75	Intermediate Similarity	NPC274678
0.75	Intermediate Similarity	NPC241891
0.75	Intermediate Similarity	NPC313650
0.75	Intermediate Similarity	NPC242628
0.75	Intermediate Similarity	NPC177576
0.75	Intermediate Similarity	NPC165212
0.75	Intermediate Similarity	NPC308689
0.75	Intermediate Similarity	NPC171831
0.75	Intermediate Similarity	NPC280616
0.7476	Intermediate Similarity	NPC265211
0.7476	Intermediate Similarity	NPC306045
0.7474	Intermediate Similarity	NPC271440
0.7474	Intermediate Similarity	NPC23453
0.7473	Intermediate Similarity	NPC243166
0.7453	Intermediate Similarity	NPC473137
0.7451	Intermediate Similarity	NPC61033
0.7451	Intermediate Similarity	NPC305603
0.7449	Intermediate Similarity	NPC92730
0.7449	Intermediate Similarity	NPC128723
0.7447	Intermediate Similarity	NPC192
0.7447	Intermediate Similarity	NPC47950
0.7426	Intermediate Similarity	NPC134829
0.7426	Intermediate Similarity	NPC211551
0.7426	Intermediate Similarity	NPC474307
0.7426	Intermediate Similarity	NPC474839
0.7419	Intermediate Similarity	NPC104216
0.74	Intermediate Similarity	NPC168829
0.7396	Intermediate Similarity	NPC20142
0.7396	Intermediate Similarity	NPC215351
0.7386	Intermediate Similarity	NPC309279
0.7379	Intermediate Similarity	NPC475282
0.7358	Intermediate Similarity	NPC261343
0.7353	Intermediate Similarity	NPC475203
0.7353	Intermediate Similarity	NPC113457
0.7353	Intermediate Similarity	NPC474376
0.7353	Intermediate Similarity	NPC302681
0.7353	Intermediate Similarity	NPC109691
0.7353	Intermediate Similarity	NPC37115
0.7353	Intermediate Similarity	NPC470700
0.7353	Intermediate Similarity	NPC39664
0.7353	Intermediate Similarity	NPC472315
0.7353	Intermediate Similarity	NPC118286
0.7353	Intermediate Similarity	NPC472316
0.7353	Intermediate Similarity	NPC39097
0.7347	Intermediate Similarity	NPC160548
0.7347	Intermediate Similarity	NPC225464
0.7347	Intermediate Similarity	NPC175852
0.7347	Intermediate Similarity	NPC210529
0.7347	Intermediate Similarity	NPC262826
0.7342	Intermediate Similarity	NPC22786
0.734	Intermediate Similarity	NPC318325
0.734	Intermediate Similarity	NPC172128
0.734	Intermediate Similarity	NPC242240
0.734	Intermediate Similarity	NPC280347
0.734	Intermediate Similarity	NPC123273
0.734	Intermediate Similarity	NPC177420
0.7333	Intermediate Similarity	NPC471188
0.7333	Intermediate Similarity	NPC111108
0.7327	Intermediate Similarity	NPC8931
0.7327	Intermediate Similarity	NPC120693
0.7327	Intermediate Similarity	NPC119860
0.7327	Intermediate Similarity	NPC288411
0.7327	Intermediate Similarity	NPC261573
0.7315	Intermediate Similarity	NPC301651
0.7315	Intermediate Similarity	NPC473556
0.7312	Intermediate Similarity	NPC477704
0.7312	Intermediate Similarity	NPC477693
0.73	Intermediate Similarity	NPC100340
0.73	Intermediate Similarity	NPC101025
0.73	Intermediate Similarity	NPC143659
0.73	Intermediate Similarity	NPC51015
0.73	Intermediate Similarity	NPC471578
0.7292	Intermediate Similarity	NPC162314
0.7292	Intermediate Similarity	NPC306884
0.7292	Intermediate Similarity	NPC3358
0.7292	Intermediate Similarity	NPC147284
0.7292	Intermediate Similarity	NPC210497
0.7292	Intermediate Similarity	NPC94139
0.729	Intermediate Similarity	NPC285350
0.729	Intermediate Similarity	NPC120280
0.729	Intermediate Similarity	NPC12656

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 NPC99482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	839
0.2-0.3	1344
0.3-0.4	3183
0.4-0.5	2151
0.5-0.6	1119
0.6-0.7	300
0.7-0.8	32
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD9294	Approved
0.7959	Intermediate Similarity	NPD5048	Discontinued
0.7938	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2859	Approved
0.7872	Intermediate Similarity	NPD2860	Approved
0.7766	Intermediate Similarity	NPD2934	Approved
0.7766	Intermediate Similarity	NPD2933	Approved
0.7677	Intermediate Similarity	NPD1237	Approved
0.7629	Intermediate Similarity	NPD3020	Approved
0.7624	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4719	Phase 2
0.7474	Intermediate Similarity	NPD3719	Approved
0.7474	Intermediate Similarity	NPD3718	Approved
0.7404	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6647	Phase 2
0.7358	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9495	Approved
0.7333	Intermediate Similarity	NPD3971	Phase 1
0.7282	Intermediate Similarity	NPD6406	Approved
0.7228	Intermediate Similarity	NPD5765	Approved
0.7228	Intermediate Similarity	NPD4658	Approved
0.7228	Intermediate Similarity	NPD4656	Approved
0.7216	Intermediate Similarity	NPD4814	Discontinued
0.7204	Intermediate Similarity	NPD4793	Discontinued
0.72	Intermediate Similarity	NPD2549	Approved
0.72	Intermediate Similarity	NPD2550	Approved
0.72	Intermediate Similarity	NPD2552	Approved
0.72	Intermediate Similarity	NPD2555	Approved
0.72	Intermediate Similarity	NPD2553	Approved
0.72	Intermediate Similarity	NPD2558	Approved
0.7172	Intermediate Similarity	NPD9612	Approved
0.7172	Intermediate Similarity	NPD9611	Approved
0.7172	Intermediate Similarity	NPD9609	Approved
0.7157	Intermediate Similarity	NPD5909	Discontinued
0.713	Intermediate Similarity	NPD2629	Approved
0.7129	Intermediate Similarity	NPD854	Approved
0.7129	Intermediate Similarity	NPD4188	Approved
0.7129	Intermediate Similarity	NPD4818	Approved
0.7129	Intermediate Similarity	NPD4189	Approved
0.7129	Intermediate Similarity	NPD4817	Approved
0.7129	Intermediate Similarity	NPD855	Approved
0.7128	Intermediate Similarity	NPD531	Approved
0.7113	Intermediate Similarity	NPD845	Approved
0.7113	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD226	Approved
0.71	Intermediate Similarity	NPD7798	Approved
0.7083	Intermediate Similarity	NPD1239	Approved
0.7071	Intermediate Similarity	NPD1875	Phase 1
0.7059	Intermediate Similarity	NPD4229	Approved
0.7059	Intermediate Similarity	NPD4231	Approved
0.7059	Intermediate Similarity	NPD3680	Approved
0.7059	Intermediate Similarity	NPD3682	Approved
0.7053	Intermediate Similarity	NPD5346	Phase 2
0.7053	Intermediate Similarity	NPD5347	Phase 2
0.7041	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD675	Discontinued
0.703	Intermediate Similarity	NPD1616	Discontinued
0.7027	Intermediate Similarity	NPD7741	Discontinued
0.7019	Intermediate Similarity	NPD6685	Approved
0.7011	Intermediate Similarity	NPD9716	Approved
0.7	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5926	Approved
0.699	Remote Similarity	NPD3046	Approved
0.699	Remote Similarity	NPD3048	Approved
0.699	Remote Similarity	NPD3047	Approved
0.6989	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3022	Approved
0.6981	Remote Similarity	NPD3021	Approved
0.697	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.697	Remote Similarity	NPD844	Approved
0.697	Remote Similarity	NPD1989	Approved
0.6961	Remote Similarity	NPD940	Approved
0.6961	Remote Similarity	NPD846	Approved
0.6957	Remote Similarity	NPD9491	Approved
0.6947	Remote Similarity	NPD1101	Approved
0.6931	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD9250	Approved
0.6903	Remote Similarity	NPD5126	Approved
0.6903	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7725	Approved
0.6903	Remote Similarity	NPD5125	Phase 3
0.6893	Remote Similarity	NPD3683	Approved
0.6893	Remote Similarity	NPD3681	Approved
0.6881	Remote Similarity	NPD6010	Discontinued
0.6875	Remote Similarity	NPD800	Approved
0.6875	Remote Similarity	NPD3091	Approved
0.6869	Remote Similarity	NPD3772	Phase 3
0.6869	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3028	Approved
0.6863	Remote Similarity	NPD1242	Phase 1
0.6857	Remote Similarity	NPD968	Approved
0.6857	Remote Similarity	NPD3526	Approved
0.6857	Remote Similarity	NPD3524	Approved
0.6857	Remote Similarity	NPD2559	Approved
0.6857	Remote Similarity	NPD2551	Approved
0.6842	Remote Similarity	NPD1282	Approved
0.6837	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD752	Approved
0.6827	Remote Similarity	NPD315	Approved
0.6827	Remote Similarity	NPD10	Approved
0.6827	Remote Similarity	NPD310	Approved
0.6827	Remote Similarity	NPD314	Approved
0.6827	Remote Similarity	NPD309	Approved
0.6827	Remote Similarity	NPD311	Approved
0.6809	Remote Similarity	NPD111	Approved
0.6804	Remote Similarity	NPD3673	Approved
0.6804	Remote Similarity	NPD3672	Approved
0.6804	Remote Similarity	NPD1089	Approved
0.6804	Remote Similarity	NPD1090	Approved
0.6804	Remote Similarity	NPD1086	Approved
0.68	Remote Similarity	NPD1809	Phase 2
0.6796	Remote Similarity	NPD1932	Approved
0.6792	Remote Similarity	NPD2342	Discontinued
0.6792	Remote Similarity	NPD9532	Phase 3
0.6789	Remote Similarity	NPD7635	Approved
0.6778	Remote Similarity	NPD227	Approved
0.6778	Remote Similarity	NPD225	Approved
0.6768	Remote Similarity	NPD1066	Discontinued
0.6768	Remote Similarity	NPD719	Approved
0.6768	Remote Similarity	NPD720	Approved
0.6759	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1564	Approved
0.6733	Remote Similarity	NPD1566	Phase 3
0.6733	Remote Similarity	NPD1565	Approved
0.6733	Remote Similarity	NPD288	Approved
0.6731	Remote Similarity	NPD1930	Approved
0.6731	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1929	Approved
0.6729	Remote Similarity	NPD2684	Approved
0.6726	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD689	Discontinued
0.67	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6049	Phase 2
0.67	Remote Similarity	NPD1693	Approved
0.6699	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5704	Approved
0.6698	Remote Similarity	NPD5705	Approved
0.6698	Remote Similarity	NPD5706	Approved
0.6697	Remote Similarity	NPD6912	Phase 3
0.6697	Remote Similarity	NPD2499	Approved
0.6697	Remote Similarity	NPD2500	Approved
0.6667	Remote Similarity	NPD5157	Phase 1
0.6667	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9538	Approved
0.6667	Remote Similarity	NPD7876	Discontinued
0.6667	Remote Similarity	NPD5159	Phase 2
0.6667	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4659	Approved
0.6667	Remote Similarity	NPD1710	Approved
0.6667	Remote Similarity	NPD9251	Approved
0.6667	Remote Similarity	NPD4750	Phase 3
0.6667	Remote Similarity	NPD1088	Approved
0.6638	Remote Similarity	NPD3974	Phase 2
0.6638	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD3092	Approved
0.6638	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7522	Discontinued
0.6636	Remote Similarity	NPD290	Approved
0.6635	Remote Similarity	NPD4119	Approved
0.663	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3095	Discontinued
0.6609	Remote Similarity	NPD5723	Approved
0.6607	Remote Similarity	NPD7508	Discontinued
0.6607	Remote Similarity	NPD4198	Discontinued
0.6606	Remote Similarity	NPD4254	Approved
0.6606	Remote Similarity	NPD4253	Approved
0.66	Remote Similarity	NPD1409	Phase 3
0.6581	Remote Similarity	NPD2561	Approved
0.6581	Remote Similarity	NPD2562	Approved
0.6577	Remote Similarity	NPD2229	Approved
0.6577	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2228	Approved
0.6577	Remote Similarity	NPD2234	Approved
0.6574	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4718	Approved
0.6574	Remote Similarity	NPD4720	Approved
0.6574	Remote Similarity	NPD4717	Approved
0.6569	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD530	Approved
0.6559	Remote Similarity	NPD942	Approved
0.6555	Remote Similarity	NPD3094	Phase 2
0.6555	Remote Similarity	NPD4103	Phase 2
0.6555	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4136	Approved
0.6552	Remote Similarity	NPD4135	Approved
0.6552	Remote Similarity	NPD4106	Approved
0.6545	Remote Similarity	NPD4572	Approved
0.6545	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4573	Approved
0.6545	Remote Similarity	NPD4571	Approved
0.6542	Remote Similarity	NPD467	Phase 1
0.6535	Remote Similarity	NPD7344	Phase 1
0.6535	Remote Similarity	NPD7343	Discovery
0.6522	Remote Similarity	NPD9490	Approved
0.6518	Remote Similarity	NPD5951	Approved
0.6514	Remote Similarity	NPD1792	Phase 2
0.6514	Remote Similarity	NPD5451	Approved
0.65	Remote Similarity	NPD6690	Approved
0.65	Remote Similarity	NPD6007	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