NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.499
LogD:	2.393
LogS:	-3.434
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.629
Fsp3:	0.8
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:	-4.719
MDCK Permeability:	3.8920421502552927e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.504
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	59.19321823120117%
Volume Distribution (VD):	1.07
Pgp-substrate:	51.19896697998047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.517
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	6.413
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.831
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.258
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.096
Carcinogencity:	0.349
Eye Corrosion:	0.008
Eye Irritation:	0.321
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC97505

Natural Product ID:	NPC97505
*Common Name:**	11,13-Dihydroivalin
IUPAC Name:	(3S,3aR,4aS,7S,8aR,9aR)-7-hydroxy-3,8a-dimethyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydro-3H-benzo[f][1]benzofuran-2-one
Synonyms:	11,13-Dihydroivalin
Standard InCHIKey:	FPEGOJNBPHXMRU-GGZSWOCBSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h9-13,16H,1,4-7H2,2-3H3/t9-,10-,11+,12-,13+,15+/m0/s1
SMILES:	C=C1C[C@@H](C[C@]2(C)C[C@@H]3[C@H](C[C@@H]12)[C@H](C)C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332646
PubChem CID:	13944074
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 [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23451797]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23861	Inula racemosa	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	6

Activity Type	# Activity
Cell Line	3
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[497824]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[497824]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[497824]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[497825]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[497825]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[497825]

☑ 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 NPC97505 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	172
0.1-0.2	1367
0.2-0.3	5206
0.3-0.4	13583
0.4-0.5	8306
0.5-0.6	5793
0.6-0.7	5964
0.7-0.8	2105
0.8-0.85	159
0.85-0.9	30
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC116620
0.9367	High Similarity	NPC223330
0.9367	High Similarity	NPC209318
0.9167	High Similarity	NPC194642
0.907	High Similarity	NPC147272
0.8974	High Similarity	NPC92489
0.8966	High Similarity	NPC148000
0.8966	High Similarity	NPC469596
0.8966	High Similarity	NPC225474
0.8929	High Similarity	NPC305029
0.8929	High Similarity	NPC181103
0.8864	High Similarity	NPC259042
0.8864	High Similarity	NPC157686
0.8837	High Similarity	NPC153853
0.881	High Similarity	NPC6979
0.881	High Similarity	NPC85698
0.8764	High Similarity	NPC256227
0.8764	High Similarity	NPC93245
0.875	High Similarity	NPC24861
0.8706	High Similarity	NPC175293
0.8675	High Similarity	NPC470948
0.8667	High Similarity	NPC473963
0.8652	High Similarity	NPC90014
0.8588	High Similarity	NPC9231
0.8588	High Similarity	NPC477920
0.8556	High Similarity	NPC473964
0.8554	High Similarity	NPC226988
0.8539	High Similarity	NPC250075
0.8523	High Similarity	NPC198054
0.85	High Similarity	NPC476601
0.8488	Intermediate Similarity	NPC470012
0.8478	Intermediate Similarity	NPC47024
0.8462	Intermediate Similarity	NPC136781
0.8434	Intermediate Similarity	NPC475951
0.8409	Intermediate Similarity	NPC475776
0.8409	Intermediate Similarity	NPC158488
0.8395	Intermediate Similarity	NPC474433
0.8387	Intermediate Similarity	NPC475958
0.8372	Intermediate Similarity	NPC185638
0.837	Intermediate Similarity	NPC16911
0.837	Intermediate Similarity	NPC78427
0.837	Intermediate Similarity	NPC476806
0.837	Intermediate Similarity	NPC216478
0.837	Intermediate Similarity	NPC476807
0.8352	Intermediate Similarity	NPC200054
0.8352	Intermediate Similarity	NPC228766
0.8352	Intermediate Similarity	NPC284518
0.8352	Intermediate Similarity	NPC165528
0.8352	Intermediate Similarity	NPC29410
0.8333	Intermediate Similarity	NPC472504
0.8333	Intermediate Similarity	NPC47853
0.8315	Intermediate Similarity	NPC186363
0.8315	Intermediate Similarity	NPC233345
0.8295	Intermediate Similarity	NPC77001
0.8295	Intermediate Similarity	NPC253618
0.828	Intermediate Similarity	NPC287676
0.8261	Intermediate Similarity	NPC253586
0.8256	Intermediate Similarity	NPC52628
0.8256	Intermediate Similarity	NPC476602
0.8242	Intermediate Similarity	NPC98639
0.8242	Intermediate Similarity	NPC470232
0.8235	Intermediate Similarity	NPC471037
0.8222	Intermediate Similarity	NPC470224
0.8222	Intermediate Similarity	NPC474436
0.8222	Intermediate Similarity	NPC49776
0.8222	Intermediate Similarity	NPC199543
0.8222	Intermediate Similarity	NPC63118
0.8214	Intermediate Similarity	NPC475743
0.8214	Intermediate Similarity	NPC473420
0.8211	Intermediate Similarity	NPC61442
0.8211	Intermediate Similarity	NPC36688
0.8202	Intermediate Similarity	NPC232202
0.8191	Intermediate Similarity	NPC163963
0.8191	Intermediate Similarity	NPC52899
0.8191	Intermediate Similarity	NPC289148
0.8182	Intermediate Similarity	NPC277771
0.8172	Intermediate Similarity	NPC89099
0.8172	Intermediate Similarity	NPC28864
0.8172	Intermediate Similarity	NPC38471
0.8172	Intermediate Similarity	NPC38296
0.8172	Intermediate Similarity	NPC471038
0.8172	Intermediate Similarity	NPC20479
0.8172	Intermediate Similarity	NPC162459
0.8172	Intermediate Similarity	NPC98837
0.8161	Intermediate Similarity	NPC12774
0.8161	Intermediate Similarity	NPC325594
0.8161	Intermediate Similarity	NPC250981
0.8152	Intermediate Similarity	NPC329910
0.814	Intermediate Similarity	NPC299963
0.814	Intermediate Similarity	NPC139566
0.8132	Intermediate Similarity	NPC475118
0.8132	Intermediate Similarity	NPC470385
0.8132	Intermediate Similarity	NPC470386
0.8105	Intermediate Similarity	NPC246736
0.8105	Intermediate Similarity	NPC164551
0.8105	Intermediate Similarity	NPC214946
0.8105	Intermediate Similarity	NPC286519
0.8105	Intermediate Similarity	NPC88203
0.8105	Intermediate Similarity	NPC76866
0.8105	Intermediate Similarity	NPC304832
0.8105	Intermediate Similarity	NPC148628
0.8085	Intermediate Similarity	NPC293866
0.8085	Intermediate Similarity	NPC477656
0.8085	Intermediate Similarity	NPC267921
0.8085	Intermediate Similarity	NPC108371
0.8085	Intermediate Similarity	NPC477655
0.8072	Intermediate Similarity	NPC35574
0.8068	Intermediate Similarity	NPC33768
0.8065	Intermediate Similarity	NPC10864
0.8046	Intermediate Similarity	NPC294438
0.8046	Intermediate Similarity	NPC329738
0.8046	Intermediate Similarity	NPC264317
0.8043	Intermediate Similarity	NPC279974
0.8043	Intermediate Similarity	NPC210214
0.8043	Intermediate Similarity	NPC183012
0.8043	Intermediate Similarity	NPC470229
0.8043	Intermediate Similarity	NPC474727
0.8043	Intermediate Similarity	NPC56369
0.8041	Intermediate Similarity	NPC102352
0.8025	Intermediate Similarity	NPC55508
0.8023	Intermediate Similarity	NPC243347
0.8023	Intermediate Similarity	NPC15091
0.8023	Intermediate Similarity	NPC194637
0.8022	Intermediate Similarity	NPC224060
0.8022	Intermediate Similarity	NPC294263
0.8022	Intermediate Similarity	NPC244356
0.8021	Intermediate Similarity	NPC216114
0.8021	Intermediate Similarity	NPC87927
0.8021	Intermediate Similarity	NPC72842
0.8	Intermediate Similarity	NPC471370
0.8	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC121218
0.8	Intermediate Similarity	NPC253886
0.8	Intermediate Similarity	NPC38642
0.8	Intermediate Similarity	NPC242666
0.8	Intermediate Similarity	NPC471371
0.8	Intermediate Similarity	NPC295276
0.8	Intermediate Similarity	NPC308824
0.8	Intermediate Similarity	NPC39683
0.8	Intermediate Similarity	NPC252614
0.7979	Intermediate Similarity	NPC119036
0.7979	Intermediate Similarity	NPC474793
0.7979	Intermediate Similarity	NPC473155
0.7979	Intermediate Similarity	NPC474724
0.7978	Intermediate Similarity	NPC4309
0.7978	Intermediate Similarity	NPC48824
0.7978	Intermediate Similarity	NPC229407
0.7978	Intermediate Similarity	NPC254572
0.7978	Intermediate Similarity	NPC250687
0.7978	Intermediate Similarity	NPC474719
0.7959	Intermediate Similarity	NPC284732
0.7959	Intermediate Similarity	NPC3316
0.7959	Intermediate Similarity	NPC230541
0.7959	Intermediate Similarity	NPC110496
0.7959	Intermediate Similarity	NPC144854
0.7959	Intermediate Similarity	NPC78966
0.7957	Intermediate Similarity	NPC104568
0.7957	Intermediate Similarity	NPC470387
0.7957	Intermediate Similarity	NPC13949
0.7957	Intermediate Similarity	NPC219353
0.7955	Intermediate Similarity	NPC329692
0.7955	Intermediate Similarity	NPC2783
0.7955	Intermediate Similarity	NPC73038
0.7952	Intermediate Similarity	NPC307865
0.7938	Intermediate Similarity	NPC202793
0.7938	Intermediate Similarity	NPC84928
0.7938	Intermediate Similarity	NPC474558
0.7938	Intermediate Similarity	NPC98603
0.7935	Intermediate Similarity	NPC474841
0.7935	Intermediate Similarity	NPC471446
0.7935	Intermediate Similarity	NPC303863
0.7935	Intermediate Similarity	NPC473434
0.7935	Intermediate Similarity	NPC57117
0.7931	Intermediate Similarity	NPC130966
0.7931	Intermediate Similarity	NPC219011
0.7931	Intermediate Similarity	NPC473299
0.7931	Intermediate Similarity	NPC470011
0.7917	Intermediate Similarity	NPC275990
0.7917	Intermediate Similarity	NPC124544
0.7917	Intermediate Similarity	NPC170615
0.7917	Intermediate Similarity	NPC476081
0.7917	Intermediate Similarity	NPC469606
0.7917	Intermediate Similarity	NPC31058
0.7917	Intermediate Similarity	NPC273005
0.7912	Intermediate Similarity	NPC250753
0.7912	Intermediate Similarity	NPC475416
0.7912	Intermediate Similarity	NPC198242
0.7912	Intermediate Similarity	NPC471747
0.7912	Intermediate Similarity	NPC211403
0.7912	Intermediate Similarity	NPC160506
0.7895	Intermediate Similarity	NPC470388
0.7895	Intermediate Similarity	NPC94906
0.7889	Intermediate Similarity	NPC470588
0.7889	Intermediate Similarity	NPC269267
0.7889	Intermediate Similarity	NPC128496
0.7889	Intermediate Similarity	NPC471043
0.7879	Intermediate Similarity	NPC275539
0.7879	Intermediate Similarity	NPC277017
0.7879	Intermediate Similarity	NPC192813
0.7879	Intermediate Similarity	NPC189075

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 NPC97505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1799
0.2-0.3	3968
0.3-0.4	2142
0.4-0.5	578
0.5-0.6	216
0.6-0.7	222
0.7-0.8	66
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8046	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8035	Phase 2
0.7912	Intermediate Similarity	NPD8034	Phase 2
0.7634	Intermediate Similarity	NPD6399	Phase 3
0.7604	Intermediate Similarity	NPD7638	Approved
0.7556	Intermediate Similarity	NPD3618	Phase 1
0.7526	Intermediate Similarity	NPD7640	Approved
0.7526	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.7442	Intermediate Similarity	NPD6115	Approved
0.7442	Intermediate Similarity	NPD6697	Approved
0.7442	Intermediate Similarity	NPD6118	Approved
0.7442	Intermediate Similarity	NPD6114	Approved
0.7368	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD4786	Approved
0.7327	Intermediate Similarity	NPD6008	Approved
0.732	Intermediate Similarity	NPD7902	Approved
0.7245	Intermediate Similarity	NPD4225	Approved
0.7209	Intermediate Similarity	NPD6117	Approved
0.7176	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5328	Approved
0.7126	Intermediate Similarity	NPD6116	Phase 1
0.7093	Intermediate Similarity	NPD3703	Phase 2
0.7065	Intermediate Similarity	NPD1694	Approved
0.703	Intermediate Similarity	NPD7632	Discontinued
0.7019	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7900	Approved
0.701	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5739	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6675	Approved
0.6989	Remote Similarity	NPD7521	Approved
0.6989	Remote Similarity	NPD5330	Approved
0.6989	Remote Similarity	NPD6409	Approved
0.6989	Remote Similarity	NPD6684	Approved
0.6989	Remote Similarity	NPD7334	Approved
0.6989	Remote Similarity	NPD7146	Approved
0.6979	Remote Similarity	NPD6079	Approved
0.6957	Remote Similarity	NPD3665	Phase 1
0.6957	Remote Similarity	NPD3666	Approved
0.6957	Remote Similarity	NPD3133	Approved
0.6952	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4697	Phase 3
0.6857	Remote Similarity	NPD7320	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6852	Remote Similarity	NPD4632	Approved
0.6852	Remote Similarity	NPD8133	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6804	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6013	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6774	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3573	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6733	Remote Similarity	NPD5696	Approved
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6705	Remote Similarity	NPD3702	Approved
0.67	Remote Similarity	NPD5221	Approved
0.67	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6637	Remote Similarity	NPD6319	Approved
0.6634	Remote Similarity	NPD5173	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6629	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6604	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5695	Phase 3
0.6598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6101	Approved
0.6593	Remote Similarity	NPD7645	Phase 2
0.6579	Remote Similarity	NPD5983	Phase 2
0.6552	Remote Similarity	NPD5777	Approved
0.6552	Remote Similarity	NPD7492	Approved
0.6548	Remote Similarity	NPD4224	Phase 2
0.6522	Remote Similarity	NPD7525	Registered
0.6517	Remote Similarity	NPD7339	Approved
0.6517	Remote Similarity	NPD6942	Approved
0.6512	Remote Similarity	NPD3698	Phase 2
0.6505	Remote Similarity	NPD5286	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD4696	Approved
0.6505	Remote Similarity	NPD5285	Approved
0.65	Remote Similarity	NPD5282	Discontinued
0.6496	Remote Similarity	NPD6616	Approved
0.6491	Remote Similarity	NPD6059	Approved
0.6491	Remote Similarity	NPD6054	Approved
0.6466	Remote Similarity	NPD7604	Phase 2
0.6466	Remote Similarity	NPD8328	Phase 3
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6098	Approved
0.6458	Remote Similarity	NPD5279	Phase 3
0.6442	Remote Similarity	NPD5223	Approved
0.6441	Remote Similarity	NPD8293	Discontinued
0.6441	Remote Similarity	NPD7078	Approved
0.6437	Remote Similarity	NPD4245	Approved
0.6437	Remote Similarity	NPD4244	Approved
0.6436	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6016	Approved
0.6429	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD6868	Approved
0.6387	Remote Similarity	NPD7736	Approved
0.6383	Remote Similarity	NPD4221	Approved
0.6383	Remote Similarity	NPD4223	Phase 3
0.6381	Remote Similarity	NPD5226	Approved
0.6381	Remote Similarity	NPD4633	Approved
0.6381	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD5225	Approved
0.6381	Remote Similarity	NPD5224	Approved
0.6379	Remote Similarity	NPD6370	Approved
0.6379	Remote Similarity	NPD5988	Approved
0.6372	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD5207	Approved
0.6356	Remote Similarity	NPD6336	Discontinued
0.6356	Remote Similarity	NPD7507	Approved
0.6344	Remote Similarity	NPD4695	Discontinued
0.6327	Remote Similarity	NPD5208	Approved
0.6325	Remote Similarity	NPD6067	Discontinued
0.6321	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD5174	Approved
0.6321	Remote Similarity	NPD5175	Approved
0.6316	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD6695	Phase 3
0.6316	Remote Similarity	NPD6313	Approved
0.6316	Remote Similarity	NPD6314	Approved
0.6304	Remote Similarity	NPD3617	Approved
0.6304	Remote Similarity	NPD3671	Phase 1
0.63	Remote Similarity	NPD5281	Approved
0.63	Remote Similarity	NPD5284	Approved
0.6293	Remote Similarity	NPD6921	Approved
0.6286	Remote Similarity	NPD1700	Approved
0.6277	Remote Similarity	NPD5369	Approved
0.6275	Remote Similarity	NPD5210	Approved
0.6275	Remote Similarity	NPD4629	Approved
0.6273	Remote Similarity	NPD4634	Approved
0.6263	Remote Similarity	NPD1695	Approved
0.6263	Remote Similarity	NPD6673	Approved
0.6263	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6080	Approved
0.6263	Remote Similarity	NPD6904	Approved
0.6262	Remote Similarity	NPD5141	Approved
0.6261	Remote Similarity	NPD7100	Approved
0.6261	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD4789	Approved
0.625	Remote Similarity	NPD4197	Approved
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6929	Approved
0.6224	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6924	Approved
0.6222	Remote Similarity	NPD6926	Approved
0.6214	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5360	Phase 3
0.6207	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4768	Approved
0.6204	Remote Similarity	NPD4767	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data