NPASS Compound

Structure

NPC473626 OpenBabel07101719512D 21 21 0 0 0 0 0 0 0 0999 V2000 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 -0.0000 -3.0000 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 0.0000 1.0000 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 -0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 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 1.7321 3.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 2 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.17
Volume:	321.88
LogP:	4.634
LogD:	4.011
LogS:	-5.046
# Rotatable Bonds:	8
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	2.402
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.596
MDCK Permeability:	2.654097079357598e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.223
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	97.8327407836914%
Volume Distribution (VD):	1.729
Pgp-substrate:	2.7099244594573975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.764
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.78
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.24
CYP2D6-substrate:	0.825
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	8.518
Half-life (T1/2):	0.401

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.271
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.921
Carcinogencity:	0.054
Eye Corrosion:	0.149
Eye Irritation:	0.88
Respiratory Toxicity:	0.34

Download Data

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

Natural Product: NPC473626

Natural Product ID:	NPC473626
*Common Name:**	Geranyloxyvanillin
IUPAC Name:	4-[(2E)-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzaldehyde
Synonyms:	Geranyloxyvanillin; O-Geranylvanillin
Standard InCHIKey:	SRLAFDUAEAXGBA-XNTDXEJSSA-N
Standard InCHI:	InChI=1S/C18H24O3/c1-14(2)6-5-7-15(3)10-11-21-17-9-8-16(13-19)12-18(17)20-4/h6,8-10,12-13H,5,7,11H2,1-4H3/b15-10+
SMILES:	COc1cc(C=O)ccc1OC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447451
PubChem CID:	6444289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO33477	Crithmum maritimum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO33477	Crithmum maritimum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254353]

☑ 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	8

Activity Type	# Activity
Individual Protein	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.914	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.105	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.43	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.707	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.335	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	3.715	n.a.	PMID[481714]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	5.742	n.a.	PMID[481714]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	85.82	ug.mL-1	PMID[481713]

☑ 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 NPC473626 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	372
0.1-0.2	2115
0.2-0.3	5613
0.3-0.4	12397
0.4-0.5	4487
0.5-0.6	5102
0.6-0.7	9495
0.7-0.8	2972
0.8-0.85	114
0.85-0.9	21
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC295317
0.928	High Similarity	NPC298268
0.9091	High Similarity	NPC225245
0.904	High Similarity	NPC117237
0.904	High Similarity	NPC203719
0.9024	High Similarity	NPC474691
0.8992	High Similarity	NPC144662
0.8983	High Similarity	NPC252004
0.888	High Similarity	NPC120066
0.8819	High Similarity	NPC304747
0.8729	High Similarity	NPC54626
0.8729	High Similarity	NPC57879
0.8678	High Similarity	NPC316062
0.8661	High Similarity	NPC154275
0.8651	High Similarity	NPC30216
0.8644	High Similarity	NPC179309
0.8594	High Similarity	NPC16651
0.8594	High Similarity	NPC32163
0.8594	High Similarity	NPC286683
0.8551	High Similarity	NPC9370
0.8551	High Similarity	NPC287495
0.855	High Similarity	NPC153453
0.8485	Intermediate Similarity	NPC288743
0.8467	Intermediate Similarity	NPC28326
0.8425	Intermediate Similarity	NPC108545
0.8421	Intermediate Similarity	NPC237330
0.8409	Intermediate Similarity	NPC50763
0.8406	Intermediate Similarity	NPC473090
0.8397	Intermediate Similarity	NPC66905
0.8397	Intermediate Similarity	NPC285776
0.839	Intermediate Similarity	NPC258171
0.8387	Intermediate Similarity	NPC159916
0.8374	Intermediate Similarity	NPC268317
0.8358	Intermediate Similarity	NPC95485
0.8358	Intermediate Similarity	NPC89504
0.8358	Intermediate Similarity	NPC38101
0.8358	Intermediate Similarity	NPC204592
0.8358	Intermediate Similarity	NPC88065
0.8358	Intermediate Similarity	NPC274613
0.8333	Intermediate Similarity	NPC183648
0.8333	Intermediate Similarity	NPC27220
0.8321	Intermediate Similarity	NPC326065
0.8321	Intermediate Similarity	NPC261759
0.832	Intermediate Similarity	NPC37858
0.831	Intermediate Similarity	NPC227980
0.8306	Intermediate Similarity	NPC185738
0.8281	Intermediate Similarity	NPC164778
0.8281	Intermediate Similarity	NPC257976
0.8281	Intermediate Similarity	NPC242372
0.8281	Intermediate Similarity	NPC21238
0.8281	Intermediate Similarity	NPC4181
0.8271	Intermediate Similarity	NPC111888
0.8264	Intermediate Similarity	NPC23332
0.8258	Intermediate Similarity	NPC299010
0.824	Intermediate Similarity	NPC277460
0.8235	Intermediate Similarity	NPC157944
0.8235	Intermediate Similarity	NPC474274
0.8226	Intermediate Similarity	NPC470860
0.8222	Intermediate Similarity	NPC139519
0.8217	Intermediate Similarity	NPC273686
0.8217	Intermediate Similarity	NPC312404
0.8217	Intermediate Similarity	NPC221798
0.8214	Intermediate Similarity	NPC293201
0.8209	Intermediate Similarity	NPC283823
0.8209	Intermediate Similarity	NPC159418
0.8203	Intermediate Similarity	NPC114298
0.8197	Intermediate Similarity	NPC165646
0.8189	Intermediate Similarity	NPC471877
0.8189	Intermediate Similarity	NPC158949
0.8175	Intermediate Similarity	NPC470962
0.8169	Intermediate Similarity	NPC294972
0.8169	Intermediate Similarity	NPC472969
0.8162	Intermediate Similarity	NPC77955
0.816	Intermediate Similarity	NPC469954
0.816	Intermediate Similarity	NPC39793
0.8156	Intermediate Similarity	NPC471590
0.8156	Intermediate Similarity	NPC136278
0.8154	Intermediate Similarity	NPC87113
0.8154	Intermediate Similarity	NPC470858
0.8148	Intermediate Similarity	NPC311339
0.8143	Intermediate Similarity	NPC469615
0.814	Intermediate Similarity	NPC141252
0.814	Intermediate Similarity	NPC11799
0.8138	Intermediate Similarity	NPC131121
0.8115	Intermediate Similarity	NPC245552
0.8115	Intermediate Similarity	NPC55300
0.8112	Intermediate Similarity	NPC476394
0.8112	Intermediate Similarity	NPC98809
0.8095	Intermediate Similarity	NPC124916
0.8092	Intermediate Similarity	NPC179777
0.8092	Intermediate Similarity	NPC127604
0.8085	Intermediate Similarity	NPC213900
0.8085	Intermediate Similarity	NPC113089
0.8085	Intermediate Similarity	NPC469683
0.808	Intermediate Similarity	NPC111225
0.8071	Intermediate Similarity	NPC299154
0.8069	Intermediate Similarity	NPC289438
0.8062	Intermediate Similarity	NPC69403
0.8062	Intermediate Similarity	NPC291189
0.8056	Intermediate Similarity	NPC473091
0.8043	Intermediate Similarity	NPC284409
0.8043	Intermediate Similarity	NPC44573
0.8043	Intermediate Similarity	NPC207516
0.8043	Intermediate Similarity	NPC325625
0.8042	Intermediate Similarity	NPC470511
0.8042	Intermediate Similarity	NPC205522
0.803	Intermediate Similarity	NPC5018
0.803	Intermediate Similarity	NPC123228
0.803	Intermediate Similarity	NPC123722
0.803	Intermediate Similarity	NPC151167
0.803	Intermediate Similarity	NPC276466
0.803	Intermediate Similarity	NPC223807
0.8028	Intermediate Similarity	NPC30890
0.8027	Intermediate Similarity	NPC180901
0.8027	Intermediate Similarity	NPC300757
0.8016	Intermediate Similarity	NPC280001
0.8015	Intermediate Similarity	NPC155098
0.8015	Intermediate Similarity	NPC280767
0.8014	Intermediate Similarity	NPC9966
0.8014	Intermediate Similarity	NPC70853
0.8014	Intermediate Similarity	NPC46161
0.8014	Intermediate Similarity	NPC239608
0.8	Intermediate Similarity	NPC278102
0.8	Intermediate Similarity	NPC244876
0.8	Intermediate Similarity	NPC220540
0.7986	Intermediate Similarity	NPC223336
0.7986	Intermediate Similarity	NPC63256
0.7986	Intermediate Similarity	NPC10304
0.7985	Intermediate Similarity	NPC282230
0.7985	Intermediate Similarity	NPC183348
0.7984	Intermediate Similarity	NPC53953
0.7984	Intermediate Similarity	NPC201777
0.7984	Intermediate Similarity	NPC303522
0.7984	Intermediate Similarity	NPC114845
0.7972	Intermediate Similarity	NPC106461
0.7972	Intermediate Similarity	NPC215932
0.7972	Intermediate Similarity	NPC40818
0.7972	Intermediate Similarity	NPC153620
0.7972	Intermediate Similarity	NPC14958
0.7972	Intermediate Similarity	NPC24257
0.7972	Intermediate Similarity	NPC110639
0.797	Intermediate Similarity	NPC226661
0.7966	Intermediate Similarity	NPC12714
0.7966	Intermediate Similarity	NPC310905
0.7958	Intermediate Similarity	NPC308006
0.7958	Intermediate Similarity	NPC275278
0.7958	Intermediate Similarity	NPC113397
0.7956	Intermediate Similarity	NPC208760
0.7955	Intermediate Similarity	NPC303680
0.7955	Intermediate Similarity	NPC475236
0.7955	Intermediate Similarity	NPC90128
0.7955	Intermediate Similarity	NPC84076
0.7955	Intermediate Similarity	NPC276014
0.7953	Intermediate Similarity	NPC205502
0.7953	Intermediate Similarity	NPC293424
0.7945	Intermediate Similarity	NPC36130
0.7945	Intermediate Similarity	NPC134905
0.7945	Intermediate Similarity	NPC75695
0.7943	Intermediate Similarity	NPC229218
0.7943	Intermediate Similarity	NPC125134
0.7943	Intermediate Similarity	NPC141817
0.7943	Intermediate Similarity	NPC169214
0.7943	Intermediate Similarity	NPC185607
0.7943	Intermediate Similarity	NPC86455
0.7943	Intermediate Similarity	NPC29536
0.7943	Intermediate Similarity	NPC137920
0.7943	Intermediate Similarity	NPC176030
0.7943	Intermediate Similarity	NPC192597
0.7941	Intermediate Similarity	NPC475468
0.7934	Intermediate Similarity	NPC151530
0.7934	Intermediate Similarity	NPC157473
0.7931	Intermediate Similarity	NPC205054
0.7931	Intermediate Similarity	NPC238366
0.7931	Intermediate Similarity	NPC474305
0.7929	Intermediate Similarity	NPC138438
0.7929	Intermediate Similarity	NPC908
0.7929	Intermediate Similarity	NPC28398
0.7929	Intermediate Similarity	NPC250597
0.7926	Intermediate Similarity	NPC15083
0.7926	Intermediate Similarity	NPC470976
0.7926	Intermediate Similarity	NPC470977
0.7926	Intermediate Similarity	NPC196979
0.7923	Intermediate Similarity	NPC256167
0.7923	Intermediate Similarity	NPC288238
0.7923	Intermediate Similarity	NPC286573
0.792	Intermediate Similarity	NPC294941
0.7917	Intermediate Similarity	NPC117463
0.7917	Intermediate Similarity	NPC85233
0.7917	Intermediate Similarity	NPC299923
0.791	Intermediate Similarity	NPC304622
0.791	Intermediate Similarity	NPC170546
0.791	Intermediate Similarity	NPC241354
0.791	Intermediate Similarity	NPC226855
0.791	Intermediate Similarity	NPC66246
0.7907	Intermediate Similarity	NPC204466
0.7902	Intermediate Similarity	NPC213482
0.7899	Intermediate Similarity	NPC90431
0.7891	Intermediate Similarity	NPC477231
0.7891	Intermediate Similarity	NPC257648
0.7891	Intermediate Similarity	NPC60211

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 NPC473626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	1063
0.2-0.3	1669
0.3-0.4	2748
0.4-0.5	1721
0.5-0.6	1021
0.6-0.7	496
0.7-0.8	85
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.904	High Similarity	NPD9494	Approved
0.8306	Intermediate Similarity	NPD5536	Phase 2
0.813	Intermediate Similarity	NPD1241	Discontinued
0.7941	Intermediate Similarity	NPD447	Suspended
0.7863	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD1358	Approved
0.7786	Intermediate Similarity	NPD3972	Approved
0.7755	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD3142	Approved
0.7737	Intermediate Similarity	NPD3140	Approved
0.7733	Intermediate Similarity	NPD3882	Suspended
0.7705	Intermediate Similarity	NPD3134	Approved
0.7703	Intermediate Similarity	NPD6386	Approved
0.7703	Intermediate Similarity	NPD6385	Approved
0.7681	Intermediate Similarity	NPD1933	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.76	Intermediate Similarity	NPD2801	Approved
0.7589	Intermediate Similarity	NPD2796	Approved
0.7582	Intermediate Similarity	NPD5494	Approved
0.7559	Intermediate Similarity	NPD5283	Phase 1
0.7554	Intermediate Similarity	NPD230	Phase 1
0.7551	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3817	Phase 2
0.7538	Intermediate Similarity	NPD9545	Approved
0.7534	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3146	Approved
0.7533	Intermediate Similarity	NPD1934	Approved
0.7532	Intermediate Similarity	NPD1247	Approved
0.7516	Intermediate Similarity	NPD919	Approved
0.7466	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD824	Approved
0.7448	Intermediate Similarity	NPD3887	Approved
0.7445	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2684	Approved
0.7434	Intermediate Similarity	NPD5353	Approved
0.7429	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD17	Approved
0.7407	Intermediate Similarity	NPD1876	Approved
0.7402	Intermediate Similarity	NPD228	Approved
0.7386	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4110	Phase 3
0.7379	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5585	Approved
0.7347	Intermediate Similarity	NPD6799	Approved
0.7325	Intermediate Similarity	NPD3926	Phase 2
0.732	Intermediate Similarity	NPD5978	Approved
0.732	Intermediate Similarity	NPD5977	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1019	Discontinued
0.7296	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1778	Approved
0.7292	Intermediate Similarity	NPD2353	Approved
0.7292	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7259	Intermediate Similarity	NPD9717	Approved
0.7259	Intermediate Similarity	NPD1608	Approved
0.723	Intermediate Similarity	NPD1511	Approved
0.7218	Intermediate Similarity	NPD5691	Approved
0.7218	Intermediate Similarity	NPD1651	Approved
0.7218	Intermediate Similarity	NPD1357	Approved
0.7215	Intermediate Similarity	NPD5242	Approved
0.7209	Intermediate Similarity	NPD7843	Approved
0.7194	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7185	Intermediate Similarity	NPD3705	Approved
0.7176	Intermediate Similarity	NPD7157	Approved
0.7172	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6166	Phase 2
0.717	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7143	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD1512	Approved
0.7124	Intermediate Similarity	NPD6873	Phase 2
0.7111	Intermediate Similarity	NPD3496	Discontinued
0.7105	Intermediate Similarity	NPD2651	Approved
0.7105	Intermediate Similarity	NPD2649	Approved
0.7103	Intermediate Similarity	NPD2935	Discontinued
0.7095	Intermediate Similarity	NPD2354	Approved
0.7095	Intermediate Similarity	NPD2309	Approved
0.7092	Intermediate Similarity	NPD411	Approved
0.7092	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD920	Approved
0.708	Intermediate Similarity	NPD4359	Approved
0.7067	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD1281	Approved
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.705	Intermediate Similarity	NPD2798	Approved
0.7047	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6233	Phase 2
0.7042	Intermediate Similarity	NPD4062	Phase 3
0.7037	Intermediate Similarity	NPD7054	Approved
0.7032	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7819	Suspended
0.702	Intermediate Similarity	NPD2186	Approved
0.7014	Intermediate Similarity	NPD2653	Approved
0.7007	Intermediate Similarity	NPD2981	Phase 2
0.7007	Intermediate Similarity	NPD1549	Phase 2
0.6994	Remote Similarity	NPD7074	Phase 3
0.6994	Remote Similarity	NPD2325	Approved
0.6994	Remote Similarity	NPD7472	Approved
0.6993	Remote Similarity	NPD1240	Approved
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD2979	Phase 3
0.6986	Remote Similarity	NPD1551	Phase 2
0.6986	Remote Similarity	NPD2438	Suspended
0.698	Remote Similarity	NPD6190	Approved
0.6978	Remote Similarity	NPD1203	Approved
0.6975	Remote Similarity	NPD2163	Approved
0.6974	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2313	Discontinued
0.6968	Remote Similarity	NPD6280	Approved
0.6968	Remote Similarity	NPD6279	Approved
0.6963	Remote Similarity	NPD9268	Approved
0.6957	Remote Similarity	NPD2982	Phase 2
0.6957	Remote Similarity	NPD2983	Phase 2
0.6954	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD290	Approved
0.6947	Remote Similarity	NPD5535	Approved
0.6939	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2346	Discontinued
0.6937	Remote Similarity	NPD6232	Discontinued
0.6929	Remote Similarity	NPD5647	Approved
0.6929	Remote Similarity	NPD9697	Approved
0.6928	Remote Similarity	NPD957	Approved
0.6923	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD8032	Phase 2
0.6918	Remote Similarity	NPD1510	Phase 2
0.6918	Remote Similarity	NPD3748	Approved
0.6912	Remote Similarity	NPD4626	Approved
0.6909	Remote Similarity	NPD7685	Pre-registration
0.6906	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD7095	Approved
0.6899	Remote Similarity	NPD2182	Approved
0.6899	Remote Similarity	NPD7075	Discontinued
0.6897	Remote Similarity	NPD2492	Phase 1
0.6897	Remote Similarity	NPD1607	Approved
0.6892	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4357	Discontinued
0.6884	Remote Similarity	NPD9269	Phase 2
0.6883	Remote Similarity	NPD7458	Discontinued
0.6883	Remote Similarity	NPD3455	Phase 2
0.6875	Remote Similarity	NPD8127	Discontinued
0.687	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7808	Phase 3
0.6866	Remote Similarity	NPD9493	Approved
0.6859	Remote Similarity	NPD6801	Discontinued
0.6857	Remote Similarity	NPD2797	Approved
0.6857	Remote Similarity	NPD3267	Approved
0.6857	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3266	Approved
0.6849	Remote Similarity	NPD743	Approved
0.6848	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1243	Approved
0.6842	Remote Similarity	NPD4661	Approved
0.6842	Remote Similarity	NPD4662	Approved
0.6839	Remote Similarity	NPD4380	Phase 2
0.6825	Remote Similarity	NPD291	Approved
0.6824	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7440	Discontinued
0.6818	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD7473	Discontinued
0.6807	Remote Similarity	NPD7038	Approved
0.6807	Remote Similarity	NPD7039	Approved
0.6807	Remote Similarity	NPD7251	Discontinued
0.6803	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4308	Phase 3
0.68	Remote Similarity	NPD1238	Approved
0.6795	Remote Similarity	NPD7110	Phase 1
0.6795	Remote Similarity	NPD958	Approved
0.6795	Remote Similarity	NPD7411	Suspended
0.6795	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3027	Phase 3
0.6781	Remote Similarity	NPD6653	Approved
0.6779	Remote Similarity	NPD2424	Discontinued
0.6779	Remote Similarity	NPD4534	Discontinued
0.6774	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5402	Approved
0.677	Remote Similarity	NPD7199	Phase 2
0.677	Remote Similarity	NPD2821	Approved
0.6763	Remote Similarity	NPD1481	Phase 2
0.6761	Remote Similarity	NPD3018	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