NPASS Compound

Structure

NPC98631 OpenBabel07101718232D 29 30 0 0 1 0 0 0 0 0999 V2000 11.2583 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 2.5981 -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 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 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 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 1 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 11.2583 0.5000 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 11.2583 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 16 23 1 6 0 0 0 17 24 1 1 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	417.668
LogP:	2.192
LogD:	2.687
LogS:	-4.202
# Rotatable Bonds:	11
TPSA:	108.61
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	3.077
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.882
MDCK Permeability:	1.480640912632225e-05
Pgp-inhibitor:	0.22
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.462
30% Bioavailability (F30%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	92.70722198486328%
Volume Distribution (VD):	0.586
Pgp-substrate:	7.984708786010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.397
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.26
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.809
CYP2D6-inhibitor:	0.316
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	12.746
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.957
Carcinogencity:	0.205
Eye Corrosion:	0.02
Eye Irritation:	0.296
Respiratory Toxicity:	0.815

Download Data

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

Natural Product: NPC98631

Natural Product ID:	NPC98631
*Common Name:**	(3S,5S)-1-(4-Hydroxy-3,5-Dimethoxyphenyl)-7-(4-Hydroxy-3-Methoxy)-3,5-Heptanediol
IUPAC Name:	(3S,5S)-1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol
Synonyms:
Standard InCHIKey:	UEKHBUNMFZUBFK-IRXDYDNUSA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-27-19-10-14(6-9-18(19)25)4-7-16(23)13-17(24)8-5-15-11-20(28-2)22(26)21(12-15)29-3/h6,9-12,16-17,23-26H,4-5,7-8,13H2,1-3H3/t16-,17-/m0/s1
SMILES:	COc1cc(CC[C@@H](C[C@H](CCc2cc(c(c(c2)OC)O)OC)O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518528
PubChem CID:	126887
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
NPO32652	zingiber ottensii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125238]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	16400.0	nM	PMID[505841]

☑ 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 NPC98631 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	371
0.1-0.2	1465
0.2-0.3	4612
0.3-0.4	12540
0.4-0.5	5581
0.5-0.6	4354
0.6-0.7	7227
0.7-0.8	4734
0.8-0.85	966
0.85-0.9	522
0.9-0.95	288
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186843
1.0	High Similarity	NPC470213
1.0	High Similarity	NPC206615
0.9918	High Similarity	NPC476968
0.9918	High Similarity	NPC170844
0.9758	High Similarity	NPC474017
0.9756	High Similarity	NPC212015
0.9752	High Similarity	NPC116907
0.9752	High Similarity	NPC208950
0.9752	High Similarity	NPC472093
0.9752	High Similarity	NPC17943
0.9752	High Similarity	NPC203133
0.9752	High Similarity	NPC57490
0.9752	High Similarity	NPC233410
0.9752	High Similarity	NPC298757
0.9752	High Similarity	NPC475169
0.9752	High Similarity	NPC221077
0.9752	High Similarity	NPC251855
0.9752	High Similarity	NPC117214
0.9752	High Similarity	NPC193544
0.968	High Similarity	NPC253105
0.968	High Similarity	NPC201587
0.9677	High Similarity	NPC472338
0.9603	High Similarity	NPC475840
0.96	High Similarity	NPC470095
0.96	High Similarity	NPC472597
0.96	High Similarity	NPC470096
0.9593	High Similarity	NPC293054
0.9593	High Similarity	NPC82679
0.9593	High Similarity	NPC282000
0.9593	High Similarity	NPC169474
0.9593	High Similarity	NPC127587
0.9593	High Similarity	NPC246620
0.9593	High Similarity	NPC124452
0.9593	High Similarity	NPC74817
0.9593	High Similarity	NPC159968
0.9593	High Similarity	NPC236791
0.9593	High Similarity	NPC324112
0.9587	High Similarity	NPC282496
0.9587	High Similarity	NPC197757
0.9587	High Similarity	NPC136319
0.9587	High Similarity	NPC228922
0.9587	High Similarity	NPC233526
0.9587	High Similarity	NPC471693
0.9528	High Similarity	NPC287745
0.9524	High Similarity	NPC184447
0.9524	High Similarity	NPC35932
0.9524	High Similarity	NPC7903
0.9524	High Similarity	NPC160991
0.9524	High Similarity	NPC16208
0.9524	High Similarity	NPC470752
0.9512	High Similarity	NPC44748
0.9512	High Similarity	NPC76451
0.9512	High Similarity	NPC78974
0.9512	High Similarity	NPC223136
0.9512	High Similarity	NPC214406
0.9512	High Similarity	NPC103823
0.9512	High Similarity	NPC18924
0.9512	High Similarity	NPC28730
0.9504	High Similarity	NPC71579
0.9504	High Similarity	NPC41562
0.9504	High Similarity	NPC473411
0.9504	High Similarity	NPC262253
0.9453	High Similarity	NPC256262
0.9449	High Similarity	NPC158331
0.9444	High Similarity	NPC309787
0.944	High Similarity	NPC218856
0.944	High Similarity	NPC469951
0.944	High Similarity	NPC469963
0.944	High Similarity	NPC470258
0.944	High Similarity	NPC190629
0.944	High Similarity	NPC3439
0.944	High Similarity	NPC285339
0.944	High Similarity	NPC210623
0.944	High Similarity	NPC273295
0.944	High Similarity	NPC202582
0.944	High Similarity	NPC226788
0.944	High Similarity	NPC222004
0.9435	High Similarity	NPC474119
0.9435	High Similarity	NPC242032
0.9435	High Similarity	NPC165045
0.9435	High Similarity	NPC210355
0.9435	High Similarity	NPC118533
0.9431	High Similarity	NPC105925
0.9431	High Similarity	NPC234400
0.9431	High Similarity	NPC148627
0.9431	High Similarity	NPC299584
0.9431	High Similarity	NPC60885
0.9431	High Similarity	NPC82483
0.9431	High Similarity	NPC265483
0.9426	High Similarity	NPC220598
0.9426	High Similarity	NPC165375
0.9421	High Similarity	NPC312675
0.9421	High Similarity	NPC49341
0.9421	High Similarity	NPC262156
0.9421	High Similarity	NPC184651
0.9421	High Similarity	NPC54872
0.9421	High Similarity	NPC343720
0.9421	High Similarity	NPC113865
0.9421	High Similarity	NPC473853
0.9421	High Similarity	NPC324571
0.9421	High Similarity	NPC470212
0.938	High Similarity	NPC16435
0.938	High Similarity	NPC306441
0.938	High Similarity	NPC472336
0.938	High Similarity	NPC472334
0.9375	High Similarity	NPC310854
0.9375	High Similarity	NPC244983
0.9375	High Similarity	NPC170694
0.9375	High Similarity	NPC326095
0.937	High Similarity	NPC175067
0.937	High Similarity	NPC204215
0.9365	High Similarity	NPC126836
0.9365	High Similarity	NPC299221
0.9365	High Similarity	NPC311680
0.9365	High Similarity	NPC51840
0.9365	High Similarity	NPC234488
0.936	High Similarity	NPC245826
0.936	High Similarity	NPC252307
0.936	High Similarity	NPC154866
0.936	High Similarity	NPC28765
0.936	High Similarity	NPC474178
0.935	High Similarity	NPC5796
0.935	High Similarity	NPC206487
0.9339	High Similarity	NPC166759
0.9339	High Similarity	NPC207613
0.9302	High Similarity	NPC94750
0.9302	High Similarity	NPC47398
0.9302	High Similarity	NPC472337
0.9302	High Similarity	NPC61946
0.9302	High Similarity	NPC470356
0.9302	High Similarity	NPC112246
0.9302	High Similarity	NPC260898
0.9302	High Similarity	NPC126409
0.9302	High Similarity	NPC474206
0.9302	High Similarity	NPC121812
0.9302	High Similarity	NPC234333
0.9302	High Similarity	NPC99572
0.9302	High Similarity	NPC112939
0.9291	High Similarity	NPC469613
0.9291	High Similarity	NPC30043
0.9291	High Similarity	NPC469625
0.9286	High Similarity	NPC10225
0.9286	High Similarity	NPC58164
0.928	High Similarity	NPC111247
0.928	High Similarity	NPC118787
0.928	High Similarity	NPC5428
0.928	High Similarity	NPC292056
0.928	High Similarity	NPC266555
0.928	High Similarity	NPC163332
0.928	High Similarity	NPC41706
0.928	High Similarity	NPC183181
0.928	High Similarity	NPC470699
0.928	High Similarity	NPC319625
0.928	High Similarity	NPC147821
0.928	High Similarity	NPC252131
0.928	High Similarity	NPC236760
0.9274	High Similarity	NPC194519
0.9268	High Similarity	NPC95168
0.9268	High Similarity	NPC121115
0.9268	High Similarity	NPC84086
0.9256	High Similarity	NPC474565
0.9256	High Similarity	NPC10932
0.9256	High Similarity	NPC247364
0.9256	High Similarity	NPC229401
0.9256	High Similarity	NPC61516
0.9256	High Similarity	NPC232084
0.9237	High Similarity	NPC22517
0.9231	High Similarity	NPC269091
0.9231	High Similarity	NPC227503
0.9231	High Similarity	NPC302701
0.9231	High Similarity	NPC474639
0.9231	High Similarity	NPC230734
0.9225	High Similarity	NPC317380
0.9219	High Similarity	NPC6451
0.9213	High Similarity	NPC242807
0.9213	High Similarity	NPC174495
0.9213	High Similarity	NPC145305
0.9213	High Similarity	NPC153739
0.9213	High Similarity	NPC42300
0.9213	High Similarity	NPC257582
0.9213	High Similarity	NPC469614
0.9213	High Similarity	NPC187998
0.9213	High Similarity	NPC241522
0.9213	High Similarity	NPC92164
0.9213	High Similarity	NPC77040
0.9213	High Similarity	NPC64201
0.9213	High Similarity	NPC469612
0.9206	High Similarity	NPC266691
0.92	High Similarity	NPC58607
0.92	High Similarity	NPC178284
0.92	High Similarity	NPC223953
0.92	High Similarity	NPC191037
0.92	High Similarity	NPC181361
0.9194	High Similarity	NPC122792
0.9194	High Similarity	NPC48990
0.9194	High Similarity	NPC114901
0.9194	High Similarity	NPC228972
0.9194	High Similarity	NPC293701
0.9174	High Similarity	NPC311595

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 NPC98631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	872
0.2-0.3	1806
0.3-0.4	2741
0.4-0.5	1647
0.5-0.6	953
0.6-0.7	643
0.7-0.8	148
0.8-0.85	11
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9918	High Similarity	NPD3027	Phase 3
0.907	High Similarity	NPD1612	Clinical (unspecified phase)
0.907	High Similarity	NPD1613	Approved
0.876	High Similarity	NPD1529	Clinical (unspecified phase)
0.8682	High Similarity	NPD1530	Clinical (unspecified phase)
0.8516	High Similarity	NPD2982	Phase 2
0.8516	High Similarity	NPD2983	Phase 2
0.8512	High Similarity	NPD228	Approved
0.8438	Intermediate Similarity	NPD2981	Phase 2
0.8397	Intermediate Similarity	NPD3018	Phase 2
0.8374	Intermediate Similarity	NPD5283	Phase 1
0.8231	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD4908	Phase 1
0.8095	Intermediate Similarity	NPD1934	Approved
0.8088	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD3620	Phase 2
0.8077	Intermediate Similarity	NPD1610	Phase 2
0.8074	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3021	Approved
0.8049	Intermediate Similarity	NPD3022	Approved
0.8047	Intermediate Similarity	NPD1548	Phase 1
0.7919	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3060	Approved
0.7852	Intermediate Similarity	NPD37	Approved
0.7846	Intermediate Similarity	NPD1357	Approved
0.7829	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD1558	Phase 1
0.7823	Intermediate Similarity	NPD1653	Approved
0.7823	Intermediate Similarity	NPD2684	Approved
0.7815	Intermediate Similarity	NPD3882	Suspended
0.7806	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6166	Phase 2
0.7806	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2801	Approved
0.7778	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4005	Discontinued
0.7746	Intermediate Similarity	NPD3540	Phase 1
0.7746	Intermediate Similarity	NPD7266	Discontinued
0.7737	Intermediate Similarity	NPD4625	Phase 3
0.7721	Intermediate Similarity	NPD2861	Phase 2
0.7717	Intermediate Similarity	NPD7843	Approved
0.7697	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD4966	Approved
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD5536	Phase 2
0.7687	Intermediate Similarity	NPD4749	Approved
0.7686	Intermediate Similarity	NPD1242	Phase 1
0.7681	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3539	Phase 1
0.7674	Intermediate Similarity	NPD7157	Approved
0.7671	Intermediate Similarity	NPD4357	Discontinued
0.7669	Intermediate Similarity	NPD3705	Approved
0.7647	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4237	Approved
0.7639	Intermediate Similarity	NPD4236	Phase 3
0.761	Intermediate Similarity	NPD7074	Phase 3
0.7603	Intermediate Similarity	NPD7124	Phase 2
0.76	Intermediate Similarity	NPD4675	Approved
0.76	Intermediate Similarity	NPD4678	Approved
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.7595	Intermediate Similarity	NPD7228	Approved
0.7571	Intermediate Similarity	NPD4060	Phase 1
0.7556	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1511	Approved
0.7547	Intermediate Similarity	NPD7054	Approved
0.7537	Intermediate Similarity	NPD1091	Approved
0.7535	Intermediate Similarity	NPD4536	Approved
0.7535	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD5177	Phase 3
0.7517	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD4380	Phase 2
0.748	Intermediate Similarity	NPD940	Approved
0.748	Intermediate Similarity	NPD846	Approved
0.746	Intermediate Similarity	NPD290	Approved
0.7451	Intermediate Similarity	NPD2978	Approved
0.7451	Intermediate Similarity	NPD2977	Approved
0.745	Intermediate Similarity	NPD1512	Approved
0.7447	Intermediate Similarity	NPD2238	Phase 2
0.7432	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6190	Approved
0.7415	Intermediate Similarity	NPD2219	Phase 1
0.7413	Intermediate Similarity	NPD6111	Discontinued
0.7407	Intermediate Similarity	NPD422	Phase 1
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.74	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4162	Approved
0.7397	Intermediate Similarity	NPD6674	Discontinued
0.7394	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD6584	Phase 3
0.7388	Intermediate Similarity	NPD6516	Phase 2
0.7388	Intermediate Similarity	NPD5846	Approved
0.7379	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD8651	Approved
0.7361	Intermediate Similarity	NPD5960	Phase 3
0.7361	Intermediate Similarity	NPD5588	Approved
0.7361	Intermediate Similarity	NPD1510	Phase 2
0.7355	Intermediate Similarity	NPD2860	Approved
0.7355	Intermediate Similarity	NPD2859	Approved
0.7347	Intermediate Similarity	NPD4628	Phase 3
0.7346	Intermediate Similarity	NPD6797	Phase 2
0.7344	Intermediate Similarity	NPD4750	Phase 3
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7339	Intermediate Similarity	NPD291	Approved
0.7338	Intermediate Similarity	NPD9494	Approved
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD1240	Approved
0.7317	Intermediate Similarity	NPD3020	Approved
0.7315	Intermediate Similarity	NPD7212	Phase 2
0.7315	Intermediate Similarity	NPD7213	Phase 3
0.7305	Intermediate Similarity	NPD5110	Phase 2
0.7305	Intermediate Similarity	NPD3145	Approved
0.7305	Intermediate Similarity	NPD3144	Approved
0.7305	Intermediate Similarity	NPD5111	Phase 2
0.7305	Intermediate Similarity	NPD5109	Approved
0.7301	Intermediate Similarity	NPD7251	Discontinued
0.7297	Intermediate Similarity	NPD5241	Discontinued
0.7296	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD5735	Approved
0.7273	Intermediate Similarity	NPD2934	Approved
0.7273	Intermediate Similarity	NPD9296	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6671	Approved
0.7267	Intermediate Similarity	NPD7447	Phase 1
0.7267	Intermediate Similarity	NPD4123	Phase 3
0.726	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7808	Phase 3
0.7256	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5058	Phase 3
0.7244	Intermediate Similarity	NPD968	Approved
0.7239	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7095	Approved
0.723	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6331	Phase 2
0.723	Intermediate Similarity	NPD3892	Phase 2
0.723	Intermediate Similarity	NPD4110	Phase 3
0.7226	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1607	Approved
0.7219	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1549	Phase 2
0.7209	Intermediate Similarity	NPD5451	Approved
0.7205	Intermediate Similarity	NPD7473	Discontinued
0.7203	Intermediate Similarity	NPD3062	Approved
0.7203	Intermediate Similarity	NPD3061	Approved
0.7203	Intermediate Similarity	NPD3059	Approved
0.7203	Intermediate Similarity	NPD943	Approved
0.7197	Intermediate Similarity	NPD4055	Discovery
0.7197	Intermediate Similarity	NPD7075	Discontinued
0.7197	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3094	Phase 2
0.7183	Intermediate Similarity	NPD6798	Discontinued
0.7181	Intermediate Similarity	NPD2677	Approved
0.7174	Intermediate Similarity	NPD6582	Phase 2
0.7174	Intermediate Similarity	NPD6583	Phase 3
0.7153	Intermediate Similarity	NPD3092	Approved
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7153	Intermediate Similarity	NPD3657	Discovery
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1375	Discontinued
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9381	Approved
0.7132	Intermediate Similarity	NPD9384	Approved
0.7124	Intermediate Similarity	NPD3686	Approved
0.7124	Intermediate Similarity	NPD3687	Approved
0.7122	Intermediate Similarity	NPD2922	Phase 1
0.7115	Intermediate Similarity	NPD1465	Phase 2
0.7115	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5494	Approved
0.7105	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5314	Approved
0.7103	Intermediate Similarity	NPD2568	Approved
0.7101	Intermediate Similarity	NPD2235	Phase 2
0.7101	Intermediate Similarity	NPD2231	Phase 2
0.7091	Intermediate Similarity	NPD7240	Approved
0.7086	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7078	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2935	Discontinued
0.7075	Intermediate Similarity	NPD6100	Approved
0.7075	Intermediate Similarity	NPD2161	Phase 2
0.7075	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD2796	Approved
0.707	Intermediate Similarity	NPD2560	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