NPASS Compound

Structure

NPC23807 OpenBabel07101719242D 28 34 0 0 1 0 0 0 0 0999 V2000 -0.1359 -2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7266 -2.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3172 -1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3749 -0.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 -1.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2738 -1.2329 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1796 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0915 -0.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6026 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4111 -1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 -1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4686 -0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6026 0.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 -0.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7366 -0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4686 -3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0556 -1.8564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5254 0.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 -1.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6904 -0.8436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 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 7 1 0 0 0 0 3 10 2 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 13 2 0 0 0 0 8 21 1 0 0 0 0 9 22 1 1 0 0 0 10 14 1 0 0 0 0 10 27 1 0 0 0 0 11 15 2 0 0 0 0 11 26 1 0 0 0 0 12 19 1 1 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 14 1 1 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 15 1 6 0 0 0 20 27 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.08
Volume:	349.084
LogP:	1.041
LogD:	0.2
LogS:	-4.012
# Rotatable Bonds:	0
TPSA:	121.14
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	6.453
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.063
MDCK Permeability:	2.344140739296563e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.386
Plasma Protein Binding (PPB):	69.50344848632812%
Volume Distribution (VD):	0.565
Pgp-substrate:	30.555130004882812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.91
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.422
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	6.216
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.643
AMES Toxicity:	0.948
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.925
Carcinogencity:	0.828
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC23807

Natural Product ID:	NPC23807
*Common Name:**	OTPVNHGOMNEPSU-KZYZBILJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OTPVNHGOMNEPSU-KZYZBILJSA-N
Standard InCHI:	InChI=1S/C20H16O8/c21-8-4-5-11-15-13(8)16(24)17-18(25-17)20(15)27-10-3-1-2-7-9(22)6-12(23)19(26-11,28-20)14(7)10/h1-5,9,12,16-18,21-24H,6H2/t9-,12+,16+,17+,18+,19+,20-/m0/s1
SMILES:	O[C@H]1C[C@@H](O)[C@@]23c4c1cccc4O[C@]1(O3)c3c(O2)ccc(c3[C@H]([C@@H]2[C@H]1O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447094
PubChem CID:	24899409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32546	ymf 1.01029	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18479163]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	54.8	%	PMID[550710]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	25.6	%	PMID[550710]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	62.3	%	PMID[550710]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	35.5	%	PMID[550710]

☑ 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 NPC23807 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	476
0.1-0.2	1661
0.2-0.3	4677
0.3-0.4	10909
0.4-0.5	7303
0.5-0.6	4725
0.6-0.7	8930
0.7-0.8	3543
0.8-0.85	447
0.85-0.9	15
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC271076
0.95	High Similarity	NPC151704
0.95	High Similarity	NPC472155
0.9433	High Similarity	NPC472154
0.9296	High Similarity	NPC173630
0.9231	High Similarity	NPC288531
0.9078	High Similarity	NPC193920
0.9007	High Similarity	NPC472151
0.8926	High Similarity	NPC306267
0.8926	High Similarity	NPC20050
0.8882	High Similarity	NPC183402
0.8824	High Similarity	NPC1253
0.8824	High Similarity	NPC100936
0.8786	High Similarity	NPC138940
0.8758	High Similarity	NPC193749
0.8733	High Similarity	NPC272552
0.8733	High Similarity	NPC233467
0.8733	High Similarity	NPC322899
0.8733	High Similarity	NPC469944
0.8733	High Similarity	NPC46283
0.8733	High Similarity	NPC44192
0.8733	High Similarity	NPC134911
0.8733	High Similarity	NPC226108
0.8726	High Similarity	NPC103633
0.8718	High Similarity	NPC11608
0.8718	High Similarity	NPC297404
0.8707	High Similarity	NPC155564
0.8707	High Similarity	NPC248053
0.8707	High Similarity	NPC102280
0.8699	High Similarity	NPC138227
0.8699	High Similarity	NPC168579
0.8699	High Similarity	NPC76176
0.8699	High Similarity	NPC469313
0.8649	High Similarity	NPC15538
0.8649	High Similarity	NPC473480
0.863	High Similarity	NPC252169
0.863	High Similarity	NPC37793
0.863	High Similarity	NPC472451
0.8609	High Similarity	NPC21902
0.8592	High Similarity	NPC188555
0.8592	High Similarity	NPC130496
0.8591	High Similarity	NPC280945
0.8591	High Similarity	NPC175976
0.8581	High Similarity	NPC125755
0.8571	High Similarity	NPC28440
0.8571	High Similarity	NPC171932
0.8562	High Similarity	NPC472353
0.8561	High Similarity	NPC40377
0.8553	High Similarity	NPC137460
0.8553	High Similarity	NPC78809
0.8542	High Similarity	NPC87777
0.8542	High Similarity	NPC262328
0.8531	High Similarity	NPC238243
0.8526	High Similarity	NPC472153
0.8523	High Similarity	NPC204770
0.8523	High Similarity	NPC263940
0.8523	High Similarity	NPC236202
0.8523	High Similarity	NPC82917
0.8523	High Similarity	NPC108811
0.8523	High Similarity	NPC202742
0.8523	High Similarity	NPC170103
0.8523	High Similarity	NPC262911
0.8523	High Similarity	NPC227902
0.8523	High Similarity	NPC294558
0.8523	High Similarity	NPC18185
0.8523	High Similarity	NPC70409
0.8523	High Similarity	NPC58190
0.8514	High Similarity	NPC277867
0.8514	High Similarity	NPC161700
0.85	High Similarity	NPC97326
0.8493	Intermediate Similarity	NPC100482
0.8493	Intermediate Similarity	NPC277331
0.8493	Intermediate Similarity	NPC210192
0.8493	Intermediate Similarity	NPC178054
0.8487	Intermediate Similarity	NPC59692
0.8477	Intermediate Similarity	NPC238140
0.8472	Intermediate Similarity	NPC197723
0.8472	Intermediate Similarity	NPC138350
0.8472	Intermediate Similarity	NPC3293
0.8472	Intermediate Similarity	NPC40664
0.8472	Intermediate Similarity	NPC475628
0.8472	Intermediate Similarity	NPC165482
0.8467	Intermediate Similarity	NPC281549
0.8462	Intermediate Similarity	NPC87696
0.8456	Intermediate Similarity	NPC99515
0.8456	Intermediate Similarity	NPC96576
0.8456	Intermediate Similarity	NPC190714
0.8452	Intermediate Similarity	NPC147743
0.8452	Intermediate Similarity	NPC73517
0.8452	Intermediate Similarity	NPC4809
0.8451	Intermediate Similarity	NPC165686
0.8451	Intermediate Similarity	NPC26080
0.8451	Intermediate Similarity	NPC85799
0.8451	Intermediate Similarity	NPC303422
0.8435	Intermediate Similarity	NPC475084
0.8435	Intermediate Similarity	NPC145319
0.8425	Intermediate Similarity	NPC106944
0.8421	Intermediate Similarity	NPC473621
0.8421	Intermediate Similarity	NPC259707
0.8421	Intermediate Similarity	NPC471403
0.8418	Intermediate Similarity	NPC120677
0.8418	Intermediate Similarity	NPC74371
0.8414	Intermediate Similarity	NPC134260
0.8411	Intermediate Similarity	NPC476969
0.8411	Intermediate Similarity	NPC211561
0.8411	Intermediate Similarity	NPC321657
0.8411	Intermediate Similarity	NPC44452
0.8411	Intermediate Similarity	NPC318373
0.8405	Intermediate Similarity	NPC272656
0.8403	Intermediate Similarity	NPC79957
0.8397	Intermediate Similarity	NPC185231
0.8397	Intermediate Similarity	NPC159526
0.8397	Intermediate Similarity	NPC106601
0.8397	Intermediate Similarity	NPC471404
0.8397	Intermediate Similarity	NPC472156
0.8397	Intermediate Similarity	NPC86630
0.8397	Intermediate Similarity	NPC205613
0.8397	Intermediate Similarity	NPC212614
0.8397	Intermediate Similarity	NPC151474
0.8392	Intermediate Similarity	NPC294166
0.8392	Intermediate Similarity	NPC115022
0.8389	Intermediate Similarity	NPC475096
0.838	Intermediate Similarity	NPC121376
0.838	Intermediate Similarity	NPC284232
0.8378	Intermediate Similarity	NPC473044
0.8369	Intermediate Similarity	NPC218003
0.8367	Intermediate Similarity	NPC257095
0.8367	Intermediate Similarity	NPC89686
0.8367	Intermediate Similarity	NPC469661
0.8367	Intermediate Similarity	NPC273932
0.8367	Intermediate Similarity	NPC471389
0.8367	Intermediate Similarity	NPC108674
0.8366	Intermediate Similarity	NPC474442
0.8365	Intermediate Similarity	NPC75944
0.8356	Intermediate Similarity	NPC471388
0.8355	Intermediate Similarity	NPC214326
0.8355	Intermediate Similarity	NPC9933
0.8355	Intermediate Similarity	NPC218041
0.8355	Intermediate Similarity	NPC260781
0.8355	Intermediate Similarity	NPC182368
0.8355	Intermediate Similarity	NPC469706
0.8355	Intermediate Similarity	NPC185955
0.8355	Intermediate Similarity	NPC225815
0.8355	Intermediate Similarity	NPC145979
0.8355	Intermediate Similarity	NPC469707
0.8345	Intermediate Similarity	NPC104167
0.8345	Intermediate Similarity	NPC234952
0.8345	Intermediate Similarity	NPC242028
0.8345	Intermediate Similarity	NPC203230
0.8344	Intermediate Similarity	NPC227516
0.8344	Intermediate Similarity	NPC20757
0.8333	Intermediate Similarity	NPC215678
0.8333	Intermediate Similarity	NPC274454
0.8322	Intermediate Similarity	NPC225445
0.8322	Intermediate Similarity	NPC25292
0.8322	Intermediate Similarity	NPC473045
0.8322	Intermediate Similarity	NPC304894
0.8322	Intermediate Similarity	NPC473108
0.8322	Intermediate Similarity	NPC15659
0.8322	Intermediate Similarity	NPC50250
0.8313	Intermediate Similarity	NPC472150
0.8311	Intermediate Similarity	NPC49542
0.8311	Intermediate Similarity	NPC5253
0.8311	Intermediate Similarity	NPC139976
0.8311	Intermediate Similarity	NPC60249
0.8311	Intermediate Similarity	NPC230718
0.8311	Intermediate Similarity	NPC128337
0.8311	Intermediate Similarity	NPC84207
0.8311	Intermediate Similarity	NPC189115
0.8311	Intermediate Similarity	NPC469559
0.8299	Intermediate Similarity	NPC262189
0.8298	Intermediate Similarity	NPC311293
0.8298	Intermediate Similarity	NPC148366
0.8291	Intermediate Similarity	NPC48880
0.8288	Intermediate Similarity	NPC211549
0.8288	Intermediate Similarity	NPC176051
0.8288	Intermediate Similarity	NPC65530
0.8288	Intermediate Similarity	NPC102904
0.8288	Intermediate Similarity	NPC103976
0.8288	Intermediate Similarity	NPC138738
0.8288	Intermediate Similarity	NPC474282
0.8288	Intermediate Similarity	NPC107551
0.8288	Intermediate Similarity	NPC59324
0.8288	Intermediate Similarity	NPC326797
0.8288	Intermediate Similarity	NPC470413
0.8278	Intermediate Similarity	NPC99183
0.8278	Intermediate Similarity	NPC174251
0.8278	Intermediate Similarity	NPC474397
0.8278	Intermediate Similarity	NPC153182
0.8276	Intermediate Similarity	NPC61946
0.8276	Intermediate Similarity	NPC164787
0.8276	Intermediate Similarity	NPC472337
0.8267	Intermediate Similarity	NPC138915
0.8267	Intermediate Similarity	NPC272619
0.8267	Intermediate Similarity	NPC11422
0.8267	Intermediate Similarity	NPC178014
0.8267	Intermediate Similarity	NPC42716
0.8267	Intermediate Similarity	NPC307466
0.8267	Intermediate Similarity	NPC474749
0.8267	Intermediate Similarity	NPC286245

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 NPC23807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	889
0.2-0.3	2031
0.3-0.4	2725
0.4-0.5	1573
0.5-0.6	939
0.6-0.7	544
0.7-0.8	57
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD3787	Discontinued
0.8194	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1613	Approved
0.8058	Intermediate Similarity	NPD1091	Approved
0.8037	Intermediate Similarity	NPD3751	Discontinued
0.7972	Intermediate Similarity	NPD2861	Phase 2
0.7935	Intermediate Similarity	NPD1653	Approved
0.7917	Intermediate Similarity	NPD4908	Phase 1
0.7917	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.7847	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD3027	Phase 3
0.7711	Intermediate Similarity	NPD7228	Approved
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7665	Intermediate Similarity	NPD7054	Approved
0.7647	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7266	Discontinued
0.7619	Intermediate Similarity	NPD7472	Approved
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7619	Intermediate Similarity	NPD4625	Phase 3
0.7574	Intermediate Similarity	NPD6797	Phase 2
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8313	Approved
0.7544	Intermediate Similarity	NPD8312	Approved
0.7529	Intermediate Similarity	NPD7251	Discontinued
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7456	Intermediate Similarity	NPD5844	Phase 1
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4749	Approved
0.7326	Intermediate Similarity	NPD7240	Approved
0.7325	Intermediate Similarity	NPD2677	Approved
0.7321	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD3705	Approved
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD6671	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD5058	Phase 3
0.7195	Intermediate Similarity	NPD1934	Approved
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD5763	Approved
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.7161	Intermediate Similarity	NPD5960	Phase 3
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7153	Intermediate Similarity	NPD968	Approved
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD7212	Phase 2
0.7125	Intermediate Similarity	NPD7213	Phase 3
0.7101	Intermediate Similarity	NPD290	Approved
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7081	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6823	Phase 2
0.7081	Intermediate Similarity	NPD7447	Phase 1
0.7078	Intermediate Similarity	NPD5735	Approved
0.707	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7157	Approved
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5588	Approved
0.7047	Intermediate Similarity	NPD6696	Suspended
0.7047	Intermediate Similarity	NPD8651	Approved
0.7044	Intermediate Similarity	NPD3750	Approved
0.7044	Intermediate Similarity	NPD3892	Phase 2
0.7043	Intermediate Similarity	NPD7696	Phase 3
0.7043	Intermediate Similarity	NPD7698	Approved
0.7043	Intermediate Similarity	NPD7697	Approved
0.7043	Intermediate Similarity	NPD7435	Discontinued
0.702	Intermediate Similarity	NPD3018	Phase 2
0.7013	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3620	Phase 2
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3496	Discontinued
0.7006	Intermediate Similarity	NPD8054	Approved
0.7006	Intermediate Similarity	NPD8053	Approved
0.7	Intermediate Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7549	Discontinued
0.6984	Remote Similarity	NPD7701	Phase 2
0.698	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7843	Approved
0.6968	Remote Similarity	NPD5124	Phase 1
0.6968	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD5494	Approved
0.6939	Remote Similarity	NPD5846	Approved
0.6939	Remote Similarity	NPD6516	Phase 2
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6929	Remote Similarity	NPD2684	Approved
0.6928	Remote Similarity	NPD7095	Approved
0.6927	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6919	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7870	Phase 2
0.6915	Remote Similarity	NPD7871	Phase 2
0.6914	Remote Similarity	NPD1511	Approved
0.6905	Remote Similarity	NPD3817	Phase 2
0.6905	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2238	Phase 2
0.6903	Remote Similarity	NPD4140	Approved
0.6899	Remote Similarity	NPD6099	Approved
0.6899	Remote Similarity	NPD6100	Approved
0.6889	Remote Similarity	NPD7906	Approved
0.6885	Remote Similarity	NPD6535	Approved
0.6885	Remote Similarity	NPD6534	Approved
0.6875	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7007	Discovery
0.6875	Remote Similarity	NPD7783	Phase 2
0.6871	Remote Similarity	NPD1357	Approved
0.6871	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD2983	Phase 2
0.6867	Remote Similarity	NPD2982	Phase 2
0.6865	Remote Similarity	NPD7699	Phase 2
0.6865	Remote Similarity	NPD7700	Phase 2
0.6862	Remote Similarity	NPD7680	Approved
0.686	Remote Similarity	NPD6232	Discontinued
0.6859	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4578	Approved
0.6854	Remote Similarity	NPD4577	Approved
0.6846	Remote Similarity	NPD1611	Approved
0.6846	Remote Similarity	NPD422	Phase 1
0.6845	Remote Similarity	NPD5929	Approved
0.6842	Remote Similarity	NPD6584	Phase 3
0.6835	Remote Similarity	NPD2154	Approved
0.6835	Remote Similarity	NPD4108	Discontinued
0.6835	Remote Similarity	NPD2155	Approved
0.6835	Remote Similarity	NPD7033	Discontinued
0.6835	Remote Similarity	NPD2156	Approved
0.6832	Remote Similarity	NPD4628	Phase 3
0.6829	Remote Similarity	NPD1512	Approved
0.6828	Remote Similarity	NPD709	Approved
0.6824	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7874	Approved
0.6821	Remote Similarity	NPD3225	Approved
0.6815	Remote Similarity	NPD6653	Approved
0.6813	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD7037	Approved
0.681	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7041	Phase 2
0.6806	Remote Similarity	NPD5283	Phase 1
0.6806	Remote Similarity	NPD1398	Phase 1
0.6802	Remote Similarity	NPD8127	Discontinued
0.68	Remote Similarity	NPD2231	Phase 2
0.68	Remote Similarity	NPD2981	Phase 2
0.68	Remote Similarity	NPD2235	Phase 2
0.6788	Remote Similarity	NPD7801	Approved
0.6783	Remote Similarity	NPD228	Approved
0.6782	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7340	Approved
0.6776	Remote Similarity	NPD3094	Phase 2
0.6772	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8151	Discontinued
0.677	Remote Similarity	NPD5061	Approved
0.677	Remote Similarity	NPD5177	Phase 3
0.677	Remote Similarity	NPD5062	Approved
0.6765	Remote Similarity	NPD7768	Phase 2

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