NPASS Compound

Structure

NPC70422 OpenBabel07101718232D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.0438 4.3378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8789 5.7842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9443 -1.5363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2607 2.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9599 1.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0875 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4665 0.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7140 4.3378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 -0.6675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8789 4.8199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 -0.6675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3472 1.5211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1271 0.0864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9604 0.0864 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7404 1.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7140 3.3735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1750 1.0265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0438 1.4449 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3790 0.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9126 1.0265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8268 2.4815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5491 2.8914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3191 1.1013 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 -2.0438 2.4092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 11 3 1 1 0 0 0 11 13 1 0 0 0 0 12 4 1 6 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 6 0 0 0 14 9 1 6 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	361.978
LogP:	2.583
LogD:	2.53
LogS:	-3.479
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	5.647
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.649
MDCK Permeability:	2.665304964466486e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.646
20% Bioavailability (F20%):	0.271
30% Bioavailability (F30%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.454
Plasma Protein Binding (PPB):	91.48638153076172%
Volume Distribution (VD):	0.933
Pgp-substrate:	6.248419284820557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.387
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	8.112
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.159
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.945
Carcinogencity:	0.236
Eye Corrosion:	0.118
Eye Irritation:	0.286
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC70422

Natural Product ID:	NPC70422
*Common Name:**	6-O-Isovaleryldihydrohelenalin
IUPAC Name:	[(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] 3-methylbutanoate
Synonyms:	6-O-Isovaleryldihydrohelenalin
Standard InCHIKey:	XOSUIROVCFABAY-QUQQNCTQSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-10(2)8-16(22)25-18-17-12(4)19(23)24-14(17)9-11(3)13-6-7-15(21)20(13,18)5/h6-7,10-14,17-18H,8-9H2,1-5H3/t11-,12+,13+,14-,17-,18+,20+/m1/s1
SMILES:	CC(CC(=O)O[C@H]1[C@H]2[C@@H](C[C@H]([C@H]3[C@@]1(C)C(=O)C=C3)C)OC(=O)[C@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452752
PubChem CID:	14656908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones

*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
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[16644542]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[16644542]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12107	Arnica montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12107	Arnica montana	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
IC50	5

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20000.0	nM	PMID[476207]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[476207]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	16634.13	nM	PMID[476208]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[476208]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	16630.0	nM	PMID[476208]

☑ 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 NPC70422 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	225
0.1-0.2	1623
0.2-0.3	7411
0.3-0.4	14200
0.4-0.5	9096
0.5-0.6	6764
0.6-0.7	2985
0.7-0.8	347
0.8-0.85	22
0.85-0.9	11
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70555
1.0	High Similarity	NPC104961
0.9524	High Similarity	NPC253144
0.9412	High Similarity	NPC74103
0.9412	High Similarity	NPC150978
0.9412	High Similarity	NPC284185
0.9412	High Similarity	NPC123177
0.9412	High Similarity	NPC70595
0.9405	High Similarity	NPC52198
0.9405	High Similarity	NPC117405
0.9195	High Similarity	NPC289004
0.8989	High Similarity	NPC185553
0.8889	High Similarity	NPC169205
0.8876	High Similarity	NPC193645
0.8876	High Similarity	NPC48803
0.8876	High Similarity	NPC90121
0.8876	High Similarity	NPC275960
0.8791	High Similarity	NPC54843
0.8791	High Similarity	NPC141191
0.8706	High Similarity	NPC161957
0.8706	High Similarity	NPC33570
0.8706	High Similarity	NPC21471
0.8511	High Similarity	NPC225353
0.8471	Intermediate Similarity	NPC39588
0.8452	Intermediate Similarity	NPC39411
0.8452	Intermediate Similarity	NPC255580
0.8421	Intermediate Similarity	NPC110989
0.8391	Intermediate Similarity	NPC238593
0.8352	Intermediate Similarity	NPC167219
0.8333	Intermediate Similarity	NPC203659
0.8256	Intermediate Similarity	NPC215294
0.8182	Intermediate Similarity	NPC107787
0.8161	Intermediate Similarity	NPC115786
0.8132	Intermediate Similarity	NPC261607
0.8132	Intermediate Similarity	NPC111114
0.8132	Intermediate Similarity	NPC300312
0.8118	Intermediate Similarity	NPC223904
0.8068	Intermediate Similarity	NPC125290
0.8068	Intermediate Similarity	NPC78089
0.8061	Intermediate Similarity	NPC291643
0.8046	Intermediate Similarity	NPC54468
0.7976	Intermediate Similarity	NPC15975
0.7976	Intermediate Similarity	NPC195785
0.7955	Intermediate Similarity	NPC165287
0.7935	Intermediate Similarity	NPC191339
0.7935	Intermediate Similarity	NPC286341
0.7927	Intermediate Similarity	NPC472956
0.7912	Intermediate Similarity	NPC12872
0.7912	Intermediate Similarity	NPC168679
0.7907	Intermediate Similarity	NPC74673
0.7907	Intermediate Similarity	NPC69271
0.7857	Intermediate Similarity	NPC472967
0.7857	Intermediate Similarity	NPC266119
0.7857	Intermediate Similarity	NPC472959
0.7857	Intermediate Similarity	NPC266159
0.7835	Intermediate Similarity	NPC477950
0.7835	Intermediate Similarity	NPC171759
0.7826	Intermediate Similarity	NPC62815
0.7816	Intermediate Similarity	NPC25684
0.7816	Intermediate Similarity	NPC301477
0.7816	Intermediate Similarity	NPC35089
0.7816	Intermediate Similarity	NPC10276
0.7816	Intermediate Similarity	NPC281949
0.7805	Intermediate Similarity	NPC470243
0.7802	Intermediate Similarity	NPC471047
0.7802	Intermediate Similarity	NPC469653
0.7802	Intermediate Similarity	NPC469631
0.7802	Intermediate Similarity	NPC475906
0.7802	Intermediate Similarity	NPC469628
0.7766	Intermediate Similarity	NPC476267
0.7755	Intermediate Similarity	NPC474747
0.7708	Intermediate Similarity	NPC108475
0.7708	Intermediate Similarity	NPC170143
0.7708	Intermediate Similarity	NPC213947
0.7701	Intermediate Similarity	NPC302426
0.7701	Intermediate Similarity	NPC290508
0.7701	Intermediate Similarity	NPC73052
0.7701	Intermediate Similarity	NPC293418
0.7701	Intermediate Similarity	NPC276356
0.7701	Intermediate Similarity	NPC6823
0.7692	Intermediate Similarity	NPC471739
0.7692	Intermediate Similarity	NPC478144
0.7692	Intermediate Similarity	NPC237540
0.7684	Intermediate Similarity	NPC474490
0.7684	Intermediate Similarity	NPC304886
0.7677	Intermediate Similarity	NPC475871
0.7677	Intermediate Similarity	NPC475945
0.766	Intermediate Similarity	NPC135776
0.7653	Intermediate Similarity	NPC474742
0.764	Intermediate Similarity	NPC475947
0.7634	Intermediate Similarity	NPC129419
0.7604	Intermediate Similarity	NPC91771
0.7604	Intermediate Similarity	NPC142529
0.7604	Intermediate Similarity	NPC126156
0.76	Intermediate Similarity	NPC474741
0.7586	Intermediate Similarity	NPC469620
0.7586	Intermediate Similarity	NPC469690
0.7579	Intermediate Similarity	NPC140543
0.7579	Intermediate Similarity	NPC148463
0.7579	Intermediate Similarity	NPC477131
0.7561	Intermediate Similarity	NPC296522
0.7561	Intermediate Similarity	NPC144511
0.7558	Intermediate Similarity	NPC476794
0.7558	Intermediate Similarity	NPC476264
0.7558	Intermediate Similarity	NPC476325
0.7558	Intermediate Similarity	NPC470240
0.7553	Intermediate Similarity	NPC133698
0.7528	Intermediate Similarity	NPC173609
0.7527	Intermediate Similarity	NPC268298
0.7526	Intermediate Similarity	NPC292133
0.75	Intermediate Similarity	NPC51507
0.75	Intermediate Similarity	NPC475873
0.75	Intermediate Similarity	NPC201658
0.75	Intermediate Similarity	NPC478145
0.7474	Intermediate Similarity	NPC473263
0.7474	Intermediate Similarity	NPC60386
0.7474	Intermediate Similarity	NPC202824
0.7474	Intermediate Similarity	NPC153590
0.7474	Intermediate Similarity	NPC308656
0.7474	Intermediate Similarity	NPC473273
0.7474	Intermediate Similarity	NPC473234
0.7474	Intermediate Similarity	NPC477361
0.7473	Intermediate Similarity	NPC155873
0.7471	Intermediate Similarity	NPC128276
0.747	Intermediate Similarity	NPC472955
0.7447	Intermediate Similarity	NPC312042
0.7444	Intermediate Similarity	NPC108045
0.7444	Intermediate Similarity	NPC318468
0.7444	Intermediate Similarity	NPC475622
0.7426	Intermediate Similarity	NPC309190
0.7426	Intermediate Similarity	NPC100487
0.7423	Intermediate Similarity	NPC477354
0.7423	Intermediate Similarity	NPC184065
0.7423	Intermediate Similarity	NPC121036
0.7423	Intermediate Similarity	NPC472674
0.7419	Intermediate Similarity	NPC226863
0.7419	Intermediate Similarity	NPC475902
0.7419	Intermediate Similarity	NPC190718
0.7416	Intermediate Similarity	NPC470241
0.7416	Intermediate Similarity	NPC471325
0.7416	Intermediate Similarity	NPC475665
0.7416	Intermediate Similarity	NPC286229
0.7416	Intermediate Similarity	NPC141810
0.7416	Intermediate Similarity	NPC42470
0.7412	Intermediate Similarity	NPC330016
0.7412	Intermediate Similarity	NPC469641
0.7412	Intermediate Similarity	NPC469643
0.7396	Intermediate Similarity	NPC469632
0.7396	Intermediate Similarity	NPC198853
0.7391	Intermediate Similarity	NPC64153
0.7391	Intermediate Similarity	NPC38576
0.7391	Intermediate Similarity	NPC304558
0.7391	Intermediate Similarity	NPC279859
0.7391	Intermediate Similarity	NPC284902
0.7391	Intermediate Similarity	NPC236692
0.7391	Intermediate Similarity	NPC309757
0.7386	Intermediate Similarity	NPC617
0.7386	Intermediate Similarity	NPC472965
0.7386	Intermediate Similarity	NPC178277
0.7386	Intermediate Similarity	NPC63649
0.7386	Intermediate Similarity	NPC264227
0.7386	Intermediate Similarity	NPC182550
0.7386	Intermediate Similarity	NPC113363
0.7386	Intermediate Similarity	NPC270126
0.7375	Intermediate Similarity	NPC469723
0.7368	Intermediate Similarity	NPC131209
0.7368	Intermediate Similarity	NPC221282
0.7368	Intermediate Similarity	NPC290651
0.7368	Intermediate Similarity	NPC20713
0.7363	Intermediate Similarity	NPC472957
0.7363	Intermediate Similarity	NPC38569
0.7363	Intermediate Similarity	NPC472958
0.7363	Intermediate Similarity	NPC475796
0.7363	Intermediate Similarity	NPC163615
0.7358	Intermediate Similarity	NPC209058
0.7356	Intermediate Similarity	NPC57744
0.7356	Intermediate Similarity	NPC474760
0.7356	Intermediate Similarity	NPC208223
0.7356	Intermediate Similarity	NPC65603
0.7356	Intermediate Similarity	NPC122264
0.7349	Intermediate Similarity	NPC199557
0.7347	Intermediate Similarity	NPC477949
0.734	Intermediate Similarity	NPC166919
0.734	Intermediate Similarity	NPC78008
0.734	Intermediate Similarity	NPC32922
0.734	Intermediate Similarity	NPC4986
0.7333	Intermediate Similarity	NPC475690
0.7326	Intermediate Similarity	NPC469678
0.7326	Intermediate Similarity	NPC226669
0.7326	Intermediate Similarity	NPC138408
0.7326	Intermediate Similarity	NPC471491
0.7326	Intermediate Similarity	NPC469669
0.7326	Intermediate Similarity	NPC193351
0.7326	Intermediate Similarity	NPC179922
0.7326	Intermediate Similarity	NPC475771
0.732	Intermediate Similarity	NPC473369
0.7312	Intermediate Similarity	NPC38885
0.7312	Intermediate Similarity	NPC72513
0.7312	Intermediate Similarity	NPC475703
0.7312	Intermediate Similarity	NPC24728

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 NPC70422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	2317
0.2-0.3	4105
0.3-0.4	1743
0.4-0.5	467
0.5-0.6	216
0.6-0.7	98
0.7-0.8	10
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8876	High Similarity	NPD1698	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5282	Discontinued
0.734	Intermediate Similarity	NPD1695	Approved
0.7333	Intermediate Similarity	NPD6435	Approved
0.7333	Intermediate Similarity	NPD5209	Approved
0.7283	Intermediate Similarity	NPD1694	Approved
0.7263	Intermediate Similarity	NPD5785	Approved
0.7115	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5368	Approved
0.7097	Intermediate Similarity	NPD5363	Approved
0.7075	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD5786	Approved
0.701	Intermediate Similarity	NPD6411	Approved
0.6957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6903	Approved
0.6857	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6804	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6101	Approved
0.6792	Remote Similarity	NPD5697	Approved
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6737	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5207	Approved
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6672	Approved
0.67	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7900	Approved
0.6697	Remote Similarity	NPD6649	Approved
0.6697	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.6602	Remote Similarity	NPD4225	Approved
0.66	Remote Similarity	NPD6399	Phase 3
0.66	Remote Similarity	NPD5778	Approved
0.66	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD7320	Approved
0.6559	Remote Similarity	NPD4252	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6617	Approved
0.6542	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD5739	Approved
0.6542	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD7128	Approved
0.6526	Remote Similarity	NPD7154	Phase 3
0.6526	Remote Similarity	NPD5362	Discontinued
0.6514	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD7983	Approved
0.6486	Remote Similarity	NPD6882	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6481	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5695	Phase 3
0.6442	Remote Similarity	NPD5696	Approved
0.6441	Remote Similarity	NPD7492	Approved
0.6437	Remote Similarity	NPD229	Approved
0.6387	Remote Similarity	NPD6616	Approved
0.6383	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5286	Approved
0.6381	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD4696	Approved
0.6379	Remote Similarity	NPD6319	Approved
0.6379	Remote Similarity	NPD6054	Approved
0.6373	Remote Similarity	NPD6001	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6079	Approved
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5694	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6333	Remote Similarity	NPD7078	Approved
0.6327	Remote Similarity	NPD4249	Approved
0.6325	Remote Similarity	NPD6016	Approved
0.6325	Remote Similarity	NPD6015	Approved
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD6673	Approved
0.63	Remote Similarity	NPD6904	Approved
0.6281	Remote Similarity	NPD7736	Approved
0.6271	Remote Similarity	NPD5988	Approved
0.6271	Remote Similarity	NPD6370	Approved
0.6263	Remote Similarity	NPD4251	Approved
0.6263	Remote Similarity	NPD4250	Approved
0.6262	Remote Similarity	NPD5226	Approved
0.6262	Remote Similarity	NPD5225	Approved
0.6262	Remote Similarity	NPD4633	Approved
0.6262	Remote Similarity	NPD5224	Approved
0.6262	Remote Similarity	NPD5211	Phase 2
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5692	Phase 3
0.6211	Remote Similarity	NPD4819	Approved
0.6211	Remote Similarity	NPD4821	Approved
0.6211	Remote Similarity	NPD4822	Approved
0.6211	Remote Similarity	NPD4820	Approved
0.6204	Remote Similarity	NPD5174	Approved
0.6204	Remote Similarity	NPD5175	Approved
0.62	Remote Similarity	NPD5208	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.619	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD5173	Approved
0.6176	Remote Similarity	NPD5693	Phase 1
0.6176	Remote Similarity	NPD6050	Approved
0.6176	Remote Similarity	NPD7515	Phase 2
0.6174	Remote Similarity	NPD6274	Approved
0.617	Remote Similarity	NPD4271	Approved
0.617	Remote Similarity	NPD4268	Approved
0.6168	Remote Similarity	NPD5223	Approved
0.6162	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3618	Phase 1
0.6161	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6147	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6139	Remote Similarity	NPD5328	Approved
0.6126	Remote Similarity	NPD6686	Approved
0.6122	Remote Similarity	NPD3133	Approved
0.6122	Remote Similarity	NPD3665	Phase 1
0.6122	Remote Similarity	NPD3666	Approved
0.6121	Remote Similarity	NPD6317	Approved
0.6106	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6059	Approved
0.6095	Remote Similarity	NPD7839	Suspended
0.6095	Remote Similarity	NPD4697	Phase 3
0.6092	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6698	Approved
0.6078	Remote Similarity	NPD46	Approved
0.6075	Remote Similarity	NPD4700	Approved
0.6068	Remote Similarity	NPD6314	Approved
0.6068	Remote Similarity	NPD6335	Approved
0.6068	Remote Similarity	NPD6313	Approved
0.6066	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6052	Approved
0.6053	Remote Similarity	NPD6053	Discontinued
0.6042	Remote Similarity	NPD4695	Discontinued
0.6034	Remote Similarity	NPD6868	Approved
0.6023	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.5983	Remote Similarity	NPD6009	Approved
0.5982	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4729	Approved
0.5982	Remote Similarity	NPD4730	Approved
0.598	Remote Similarity	NPD5370	Suspended
0.598	Remote Similarity	NPD4753	Phase 2
0.596	Remote Similarity	NPD3668	Phase 3
0.595	Remote Similarity	NPD8328	Phase 3
0.5943	Remote Similarity	NPD7732	Phase 3
0.5943	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7838	Discovery
0.5918	Remote Similarity	NPD3667	Approved
0.5917	Remote Similarity	NPD5983	Phase 2
0.5909	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7341	Phase 2
0.5893	Remote Similarity	NPD6412	Phase 2
0.5893	Remote Similarity	NPD6614	Approved
0.5877	Remote Similarity	NPD5250	Approved
0.5877	Remote Similarity	NPD5251	Approved
0.5877	Remote Similarity	NPD5247	Approved
0.5877	Remote Similarity	NPD5249	Phase 3
0.5877	Remote Similarity	NPD5248	Approved
0.5865	Remote Similarity	NPD8035	Phase 2
0.5865	Remote Similarity	NPD8034	Phase 2
0.5865	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5332	Approved
0.5859	Remote Similarity	NPD5331	Approved
0.5849	Remote Similarity	NPD5654	Approved
0.5842	Remote Similarity	NPD6422	Discontinued
0.5842	Remote Similarity	NPD4623	Approved
0.5842	Remote Similarity	NPD5690	Phase 2
0.5842	Remote Similarity	NPD4519	Discontinued

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