NPASS Compound

Structure

NPC469568 OpenBabel07101719512D 24 24 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 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 0.8660 2.5000 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 -0.0000 -2.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 3 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 7 1 0 0 0 0 2 12 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	362.625
LogP:	4.374
LogD:	2.542
LogS:	-3.36
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	3.656
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.657
MDCK Permeability:	2.1815738364239223e-05
Pgp-inhibitor:	0.354
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.16
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	96.78634643554688%
Volume Distribution (VD):	1.579
Pgp-substrate:	4.819256782531738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.88
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.919
CYP2C19-substrate:	0.259
CYP2C9-inhibitor:	0.911
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.891
CYP2D6-substrate:	0.491
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	14.731
Half-life (T1/2):	0.41

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.592
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.494
Skin Sensitization:	0.833
Carcinogencity:	0.291
Eye Corrosion:	0.028
Eye Irritation:	0.907
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC469568

Natural Product ID:	NPC469568
*Common Name:**	Altaicalarin B
IUPAC Name:	[2-(2,3-dihydroxy-4-methylphenyl)-6-methylhepta-1,5-dien-3-yl] (Z)-2-methylbut-2-enoate
Synonyms:	altaicalarin B
Standard InCHIKey:	SCWFHGJMMYKSLU-QPEQYQDCSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-7-13(4)20(23)24-17(11-8-12(2)3)15(6)16-10-9-14(5)18(21)19(16)22/h7-10,17,21-22H,6,11H2,1-5H3/b13-7-
SMILES:	C/C=C(/C)C(=O)OC(CC=C(C)C)C(=C)c1ccc(C)c(c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087668
PubChem CID:	46186371
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO40189	Ligularia rumicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30212198]
NPO12711	Ligularia altaica	Species	Asteraceae	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
EC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	10.8	ug.mL-1	PMID[574037]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	11.8	ug.mL-1	PMID[574037]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[574037]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	15.9	ug.mL-1	PMID[574037]

☑ 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 NPC469568 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	242
0.1-0.2	1172
0.2-0.3	3150
0.3-0.4	7851
0.4-0.5	10950
0.5-0.6	5329
0.6-0.7	10655
0.7-0.8	3218
0.8-0.85	108
0.85-0.9	21
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8917	High Similarity	NPC309434
0.8898	High Similarity	NPC41851
0.8862	High Similarity	NPC327070
0.878	High Similarity	NPC147654
0.876	High Similarity	NPC203124
0.875	High Similarity	NPC281277
0.871	High Similarity	NPC325301
0.8699	High Similarity	NPC470849
0.8699	High Similarity	NPC470848
0.8667	High Similarity	NPC233669
0.8593	High Similarity	NPC469564
0.8583	High Similarity	NPC261453
0.8583	High Similarity	NPC328593
0.8583	High Similarity	NPC33749
0.8571	High Similarity	NPC26615
0.8537	High Similarity	NPC263386
0.8537	High Similarity	NPC141791
0.8512	High Similarity	NPC474967
0.85	High Similarity	NPC95381
0.85	High Similarity	NPC190212
0.85	High Similarity	NPC264558
0.8485	Intermediate Similarity	NPC106406
0.8455	Intermediate Similarity	NPC206205
0.8409	Intermediate Similarity	NPC168799
0.8409	Intermediate Similarity	NPC155209
0.8397	Intermediate Similarity	NPC318799
0.8397	Intermediate Similarity	NPC198388
0.8387	Intermediate Similarity	NPC160235
0.8374	Intermediate Similarity	NPC175799
0.8374	Intermediate Similarity	NPC610
0.8374	Intermediate Similarity	NPC200988
0.8374	Intermediate Similarity	NPC65791
0.8374	Intermediate Similarity	NPC145023
0.8358	Intermediate Similarity	NPC475111
0.8346	Intermediate Similarity	NPC135127
0.8346	Intermediate Similarity	NPC212541
0.8346	Intermediate Similarity	NPC474275
0.8346	Intermediate Similarity	NPC224208
0.8333	Intermediate Similarity	NPC18074
0.8333	Intermediate Similarity	NPC226250
0.8333	Intermediate Similarity	NPC25581
0.8333	Intermediate Similarity	NPC5419
0.8333	Intermediate Similarity	NPC61
0.832	Intermediate Similarity	NPC328485
0.8306	Intermediate Similarity	NPC275519
0.8306	Intermediate Similarity	NPC86198
0.8284	Intermediate Similarity	NPC254832
0.8284	Intermediate Similarity	NPC29317
0.8284	Intermediate Similarity	NPC176102
0.8284	Intermediate Similarity	NPC229638
0.8284	Intermediate Similarity	NPC71108
0.8284	Intermediate Similarity	NPC267539
0.8284	Intermediate Similarity	NPC204257
0.8281	Intermediate Similarity	NPC146886
0.8281	Intermediate Similarity	NPC60517
0.8281	Intermediate Similarity	NPC20443
0.8279	Intermediate Similarity	NPC217472
0.8271	Intermediate Similarity	NPC239855
0.8271	Intermediate Similarity	NPC157478
0.8271	Intermediate Similarity	NPC200422
0.8271	Intermediate Similarity	NPC295406
0.8271	Intermediate Similarity	NPC289572
0.8268	Intermediate Similarity	NPC477151
0.8268	Intermediate Similarity	NPC132518
0.8244	Intermediate Similarity	NPC477293
0.8244	Intermediate Similarity	NPC226855
0.8244	Intermediate Similarity	NPC229784
0.8244	Intermediate Similarity	NPC477294
0.824	Intermediate Similarity	NPC109371
0.824	Intermediate Similarity	NPC470214
0.824	Intermediate Similarity	NPC470215
0.824	Intermediate Similarity	NPC70084
0.8231	Intermediate Similarity	NPC476873
0.8226	Intermediate Similarity	NPC122117
0.8222	Intermediate Similarity	NPC154485
0.8222	Intermediate Similarity	NPC471872
0.8209	Intermediate Similarity	NPC886
0.8209	Intermediate Similarity	NPC34293
0.8209	Intermediate Similarity	NPC287597
0.8195	Intermediate Similarity	NPC473285
0.8189	Intermediate Similarity	NPC472271
0.8189	Intermediate Similarity	NPC322332
0.8168	Intermediate Similarity	NPC232880
0.8162	Intermediate Similarity	NPC126206
0.8154	Intermediate Similarity	NPC213552
0.8154	Intermediate Similarity	NPC118584
0.8154	Intermediate Similarity	NPC120225
0.8145	Intermediate Similarity	NPC123559
0.8143	Intermediate Similarity	NPC163898
0.8134	Intermediate Similarity	NPC254398
0.813	Intermediate Similarity	NPC197513
0.812	Intermediate Similarity	NPC219677
0.8116	Intermediate Similarity	NPC477279
0.8116	Intermediate Similarity	NPC38473
0.811	Intermediate Similarity	NPC204466
0.8102	Intermediate Similarity	NPC68092
0.8102	Intermediate Similarity	NPC476383
0.8102	Intermediate Similarity	NPC197316
0.8102	Intermediate Similarity	NPC64141
0.8102	Intermediate Similarity	NPC89105
0.8102	Intermediate Similarity	NPC472350
0.8102	Intermediate Similarity	NPC81515
0.8099	Intermediate Similarity	NPC236166
0.8095	Intermediate Similarity	NPC477803
0.8095	Intermediate Similarity	NPC98748
0.8092	Intermediate Similarity	NPC158654
0.8088	Intermediate Similarity	NPC476699
0.8088	Intermediate Similarity	NPC471665
0.8088	Intermediate Similarity	NPC471664
0.8088	Intermediate Similarity	NPC156892
0.8077	Intermediate Similarity	NPC67951
0.8077	Intermediate Similarity	NPC289459
0.8074	Intermediate Similarity	NPC67247
0.8074	Intermediate Similarity	NPC204582
0.8074	Intermediate Similarity	NPC471883
0.8071	Intermediate Similarity	NPC471763
0.8071	Intermediate Similarity	NPC469615
0.806	Intermediate Similarity	NPC473924
0.8058	Intermediate Similarity	NPC67467
0.8058	Intermediate Similarity	NPC477277
0.8058	Intermediate Similarity	NPC477278
0.8047	Intermediate Similarity	NPC70752
0.8043	Intermediate Similarity	NPC303683
0.8043	Intermediate Similarity	NPC205751
0.8043	Intermediate Similarity	NPC476819
0.8043	Intermediate Similarity	NPC473799
0.8043	Intermediate Similarity	NPC474875
0.8043	Intermediate Similarity	NPC471875
0.8043	Intermediate Similarity	NPC179505
0.8043	Intermediate Similarity	NPC289690
0.8043	Intermediate Similarity	NPC295492
0.8043	Intermediate Similarity	NPC26241
0.8043	Intermediate Similarity	NPC475530
0.8043	Intermediate Similarity	NPC288452
0.8043	Intermediate Similarity	NPC476820
0.8043	Intermediate Similarity	NPC156709
0.8043	Intermediate Similarity	NPC274891
0.8033	Intermediate Similarity	NPC228609
0.8031	Intermediate Similarity	NPC202474
0.803	Intermediate Similarity	NPC478215
0.803	Intermediate Similarity	NPC109275
0.8029	Intermediate Similarity	NPC260425
0.8029	Intermediate Similarity	NPC281780
0.8029	Intermediate Similarity	NPC476376
0.8029	Intermediate Similarity	NPC78363
0.8015	Intermediate Similarity	NPC475695
0.8015	Intermediate Similarity	NPC252095
0.8015	Intermediate Similarity	NPC18646
0.8014	Intermediate Similarity	NPC469683
0.8	Intermediate Similarity	NPC288945
0.8	Intermediate Similarity	NPC246704
0.8	Intermediate Similarity	NPC475468
0.8	Intermediate Similarity	NPC85565
0.8	Intermediate Similarity	NPC285550
0.7986	Intermediate Similarity	NPC9218
0.7986	Intermediate Similarity	NPC476377
0.7986	Intermediate Similarity	NPC134405
0.7986	Intermediate Similarity	NPC476385
0.7986	Intermediate Similarity	NPC47471
0.7985	Intermediate Similarity	NPC142530
0.7985	Intermediate Similarity	NPC473777
0.7971	Intermediate Similarity	NPC219428
0.7971	Intermediate Similarity	NPC152942
0.7971	Intermediate Similarity	NPC205195
0.7971	Intermediate Similarity	NPC171134
0.7971	Intermediate Similarity	NPC37250
0.7971	Intermediate Similarity	NPC182249
0.7971	Intermediate Similarity	NPC302857
0.7971	Intermediate Similarity	NPC321184
0.7971	Intermediate Similarity	NPC321638
0.7971	Intermediate Similarity	NPC328273
0.7971	Intermediate Similarity	NPC142703
0.7971	Intermediate Similarity	NPC278068
0.7971	Intermediate Similarity	NPC220942
0.797	Intermediate Similarity	NPC30174
0.797	Intermediate Similarity	NPC48315
0.797	Intermediate Similarity	NPC83062
0.7969	Intermediate Similarity	NPC322569
0.7967	Intermediate Similarity	NPC131530
0.7958	Intermediate Similarity	NPC84786
0.7958	Intermediate Similarity	NPC268515
0.7958	Intermediate Similarity	NPC40222
0.7956	Intermediate Similarity	NPC470733
0.7956	Intermediate Similarity	NPC157554
0.7956	Intermediate Similarity	NPC470572
0.7956	Intermediate Similarity	NPC471988
0.7955	Intermediate Similarity	NPC66331
0.7955	Intermediate Similarity	NPC257947
0.7953	Intermediate Similarity	NPC241634
0.7943	Intermediate Similarity	NPC183824
0.7941	Intermediate Similarity	NPC471110
0.7941	Intermediate Similarity	NPC474895
0.7941	Intermediate Similarity	NPC476387
0.7941	Intermediate Similarity	NPC249791
0.7941	Intermediate Similarity	NPC119060
0.7941	Intermediate Similarity	NPC237594
0.7939	Intermediate Similarity	NPC132921
0.7939	Intermediate Similarity	NPC280767
0.7937	Intermediate Similarity	NPC278652
0.7929	Intermediate Similarity	NPC265648

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 NPC469568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	788
0.2-0.3	1685
0.3-0.4	2743
0.4-0.5	1905
0.5-0.6	1220
0.6-0.7	540
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8102	Intermediate Similarity	NPD7266	Discontinued
0.7868	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD6190	Approved
0.7692	Intermediate Similarity	NPD3496	Discontinued
0.7676	Intermediate Similarity	NPD8166	Discontinued
0.7615	Intermediate Similarity	NPD1778	Approved
0.7615	Intermediate Similarity	NPD4626	Approved
0.7574	Intermediate Similarity	NPD3027	Phase 3
0.7538	Intermediate Similarity	NPD5691	Approved
0.7519	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD9545	Approved
0.7458	Intermediate Similarity	NPD844	Approved
0.744	Intermediate Similarity	NPD3021	Approved
0.744	Intermediate Similarity	NPD3022	Approved
0.7434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1653	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1613	Approved
0.7323	Intermediate Similarity	NPD228	Approved
0.731	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD826	Approved
0.7286	Intermediate Similarity	NPD825	Approved
0.7286	Intermediate Similarity	NPD4060	Phase 1
0.725	Intermediate Similarity	NPD288	Approved
0.7246	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1934	Approved
0.7234	Intermediate Similarity	NPD447	Suspended
0.7222	Intermediate Similarity	NPD5763	Approved
0.7222	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5762	Approved
0.7185	Intermediate Similarity	NPD9269	Phase 2
0.7176	Intermediate Similarity	NPD9493	Approved
0.7174	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4750	Phase 3
0.7162	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2935	Discontinued
0.7152	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD1358	Approved
0.7115	Intermediate Similarity	NPD6234	Discontinued
0.7114	Intermediate Similarity	NPD2532	Approved
0.7114	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2533	Approved
0.7114	Intermediate Similarity	NPD2534	Approved
0.7111	Intermediate Similarity	NPD422	Phase 1
0.7103	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6005	Phase 3
0.7103	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6004	Phase 3
0.7103	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD4198	Discontinued
0.7099	Intermediate Similarity	NPD6671	Approved
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3134	Approved
0.7063	Intermediate Similarity	NPD6653	Approved
0.705	Intermediate Similarity	NPD5736	Approved
0.705	Intermediate Similarity	NPD9494	Approved
0.705	Intermediate Similarity	NPD2861	Phase 2
0.7042	Intermediate Similarity	NPD943	Approved
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7034	Intermediate Similarity	NPD6032	Approved
0.7021	Intermediate Similarity	NPD3764	Approved
0.7021	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4749	Approved
0.7007	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7635	Approved
0.6993	Remote Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD555	Phase 2
0.6993	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5536	Phase 2
0.6987	Remote Similarity	NPD3882	Suspended
0.6986	Remote Similarity	NPD2346	Discontinued
0.6985	Remote Similarity	NPD3705	Approved
0.6985	Remote Similarity	NPD1091	Approved
0.6981	Remote Similarity	NPD6232	Discontinued
0.6978	Remote Similarity	NPD257	Approved
0.6978	Remote Similarity	NPD258	Approved
0.6974	Remote Similarity	NPD3687	Approved
0.6974	Remote Similarity	NPD3686	Approved
0.6968	Remote Similarity	NPD2801	Approved
0.6966	Remote Similarity	NPD7033	Discontinued
0.6964	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9384	Approved
0.6963	Remote Similarity	NPD9381	Approved
0.6959	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6696	Suspended
0.6934	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD1511	Approved
0.6928	Remote Similarity	NPD3226	Approved
0.6923	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD9570	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD5404	Approved
0.6918	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD3818	Discontinued
0.6906	Remote Similarity	NPD2797	Approved
0.6903	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD411	Approved
0.6899	Remote Similarity	NPD2067	Discontinued
0.6894	Remote Similarity	NPD2629	Approved
0.6894	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6166	Phase 2
0.6892	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6674	Discontinued
0.6892	Remote Similarity	NPD1652	Phase 2
0.689	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD9268	Approved
0.6887	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9622	Approved
0.688	Remote Similarity	NPD940	Approved
0.688	Remote Similarity	NPD846	Approved
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD4965	Approved
0.6875	Remote Similarity	NPD290	Approved
0.6861	Remote Similarity	NPD1611	Approved
0.686	Remote Similarity	NPD845	Approved
0.6857	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD259	Phase 1
0.6853	Remote Similarity	NPD6663	Approved
0.6852	Remote Similarity	NPD7473	Discontinued
0.6849	Remote Similarity	NPD4308	Phase 3
0.6849	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1512	Approved
0.6838	Remote Similarity	NPD5125	Phase 3
0.6838	Remote Similarity	NPD5126	Approved
0.6835	Remote Similarity	NPD3225	Approved
0.6835	Remote Similarity	NPD7075	Discontinued
0.6831	Remote Similarity	NPD4625	Phase 3
0.6831	Remote Similarity	NPD7095	Approved
0.6829	Remote Similarity	NPD7074	Phase 3
0.6825	Remote Similarity	NPD6647	Phase 2
0.6824	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2684	Approved
0.6818	Remote Similarity	NPD3111	Phase 1
0.6818	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5283	Phase 1
0.6815	Remote Similarity	NPD5402	Approved
0.6812	Remote Similarity	NPD9717	Approved
0.681	Remote Similarity	NPD7228	Approved
0.6809	Remote Similarity	NPD2237	Approved
0.6806	Remote Similarity	NPD3620	Phase 2
0.6806	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD969	Suspended
0.6791	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3094	Phase 2
0.6786	Remote Similarity	NPD1470	Approved
0.6783	Remote Similarity	NPD3268	Approved
0.6783	Remote Similarity	NPD7985	Registered
0.6783	Remote Similarity	NPD2313	Discontinued
0.6774	Remote Similarity	NPD6599	Discontinued
0.6774	Remote Similarity	NPD4380	Phase 2
0.6768	Remote Similarity	NPD7054	Approved
0.6767	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1357	Approved
0.6765	Remote Similarity	NPD5585	Approved
0.6761	Remote Similarity	NPD4908	Phase 1
0.6759	Remote Similarity	NPD4340	Discontinued
0.6752	Remote Similarity	NPD1465	Phase 2
0.6752	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2859	Approved
0.6748	Remote Similarity	NPD2860	Approved
0.6747	Remote Similarity	NPD6559	Discontinued
0.6746	Remote Similarity	NPD8150	Discontinued
0.6744	Remote Similarity	NPD2342	Discontinued
0.6744	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7843	Approved
0.6739	Remote Similarity	NPD1201	Approved
0.6739	Remote Similarity	NPD3092	Approved
0.6738	Remote Similarity	NPD9619	Approved
0.6738	Remote Similarity	NPD9621	Approved
0.6738	Remote Similarity	NPD9620	Approved
0.6738	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6233	Phase 2
0.6736	Remote Similarity	NPD4248	Discontinued
0.6733	Remote Similarity	NPD3750	Approved
0.6732	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7472	Approved
0.672	Remote Similarity	NPD3020	Approved
0.6719	Remote Similarity	NPD9697	Approved
0.6718	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7157	Approved
0.6715	Remote Similarity	NPD17	Approved
0.6714	Remote Similarity	NPD1283	Approved
0.6713	Remote Similarity	NPD5952	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