NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	254.401
LogP:	3.044
LogD:	2.894
LogS:	-3.654
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.668
Synthetic Accessibility Score:	4.316
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.665
MDCK Permeability:	1.5260557120200247e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.734
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.454
Plasma Protein Binding (PPB):	65.2746810913086%
Volume Distribution (VD):	1.528
Pgp-substrate:	24.701295852661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.257
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.711
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	6.222
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.116
Carcinogencity:	0.263
Eye Corrosion:	0.799
Eye Irritation:	0.976
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC68656

Natural Product ID:	NPC68656
*Common Name:**	Isocyperol
IUPAC Name:	(2R,4aS,7R)-4a-methyl-1-methylidene-7-prop-1-en-2-yl-2,3,4,5,6,7,8,8a-octahydronaphthalen-2-ol
Synonyms:	Isocyperol
Standard InCHIKey:	CZFHAODYOVXPIQ-FFHGMXDLSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12-14,16H,1,3,5-9H2,2,4H3/t12-,13?,14-,15+/m1/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(C)CC[C@H](C(=C)C2C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489542
PubChem CID:	44576209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)90945-1]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24704449]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26967731]
NPO23832	Cyclea sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23832	Cyclea sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23832	Cyclea sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23832	Cyclea sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	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	1
Others	7

Activity Type	# Activity
Cell Line	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-28.9	%	PMID[453817]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-5.3	%	PMID[453817]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-11.9	%	PMID[453817]
NPT2	Others	Unspecified		Inhibition	=	96.8	%	PMID[453817]
NPT2	Others	Unspecified		Inhibition	=	10.3	%	PMID[453817]
NPT2	Others	Unspecified		Inhibition	=	64.4	%	PMID[453817]
NPT2	Others	Unspecified		Inhibition	=	23.9	%	PMID[453817]
NPT2	Others	Unspecified		IC50	=	21000.0	nM	PMID[453817]

☑ 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 NPC68656 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	196
0.1-0.2	2048
0.2-0.3	10005
0.3-0.4	15418
0.4-0.5	6941
0.5-0.6	5206
0.6-0.7	2237
0.7-0.8	553
0.8-0.85	57
0.85-0.9	30
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9672	High Similarity	NPC475897
0.9365	High Similarity	NPC245795
0.9365	High Similarity	NPC276616
0.9194	High Similarity	NPC258595
0.9048	High Similarity	NPC473929
0.9032	High Similarity	NPC144650
0.9032	High Similarity	NPC101128
0.8923	High Similarity	NPC9942
0.8906	High Similarity	NPC269077
0.8906	High Similarity	NPC253303
0.8906	High Similarity	NPC139207
0.8906	High Similarity	NPC185874
0.8889	High Similarity	NPC208198
0.8889	High Similarity	NPC11555
0.8889	High Similarity	NPC282619
0.8889	High Similarity	NPC60837
0.8889	High Similarity	NPC172613
0.8889	High Similarity	NPC2728
0.8788	High Similarity	NPC283316
0.8769	High Similarity	NPC244790
0.8769	High Similarity	NPC96484
0.8551	High Similarity	NPC185536
0.8551	High Similarity	NPC144075
0.8525	High Similarity	NPC189290
0.8525	High Similarity	NPC474769
0.8507	High Similarity	NPC45296
0.85	High Similarity	NPC264779
0.8485	Intermediate Similarity	NPC266578
0.8462	Intermediate Similarity	NPC476406
0.8429	Intermediate Similarity	NPC38141
0.8406	Intermediate Similarity	NPC469593
0.8406	Intermediate Similarity	NPC476366
0.8406	Intermediate Similarity	NPC469534
0.8406	Intermediate Similarity	NPC476736
0.8406	Intermediate Similarity	NPC469533
0.8406	Intermediate Similarity	NPC201048
0.8406	Intermediate Similarity	NPC306727
0.8382	Intermediate Similarity	NPC167706
0.8382	Intermediate Similarity	NPC301226
0.8382	Intermediate Similarity	NPC111234
0.8382	Intermediate Similarity	NPC164045
0.8358	Intermediate Similarity	NPC474248
0.8358	Intermediate Similarity	NPC234511
0.8333	Intermediate Similarity	NPC308522
0.8333	Intermediate Similarity	NPC74885
0.831	Intermediate Similarity	NPC307336
0.831	Intermediate Similarity	NPC212241
0.831	Intermediate Similarity	NPC257191
0.831	Intermediate Similarity	NPC138502
0.831	Intermediate Similarity	NPC119355
0.831	Intermediate Similarity	NPC248830
0.831	Intermediate Similarity	NPC260301
0.831	Intermediate Similarity	NPC331618
0.831	Intermediate Similarity	NPC470758
0.831	Intermediate Similarity	NPC470711
0.8261	Intermediate Similarity	NPC195489
0.8261	Intermediate Similarity	NPC472506
0.8261	Intermediate Similarity	NPC95165
0.8261	Intermediate Similarity	NPC182717
0.8261	Intermediate Similarity	NPC211009
0.8235	Intermediate Similarity	NPC92801
0.8235	Intermediate Similarity	NPC34834
0.8209	Intermediate Similarity	NPC471238
0.8209	Intermediate Similarity	NPC208999
0.8194	Intermediate Similarity	NPC472499
0.8194	Intermediate Similarity	NPC472500
0.8194	Intermediate Similarity	NPC472342
0.8194	Intermediate Similarity	NPC472501
0.8194	Intermediate Similarity	NPC301707
0.8182	Intermediate Similarity	NPC202017
0.8169	Intermediate Similarity	NPC470749
0.8169	Intermediate Similarity	NPC265588
0.8169	Intermediate Similarity	NPC253190
0.8154	Intermediate Similarity	NPC96793
0.8154	Intermediate Similarity	NPC323424
0.8143	Intermediate Similarity	NPC49168
0.8143	Intermediate Similarity	NPC5046
0.8143	Intermediate Similarity	NPC254509
0.8143	Intermediate Similarity	NPC62657
0.8143	Intermediate Similarity	NPC145552
0.8143	Intermediate Similarity	NPC196358
0.8143	Intermediate Similarity	NPC308440
0.8143	Intermediate Similarity	NPC25511
0.8143	Intermediate Similarity	NPC100334
0.8143	Intermediate Similarity	NPC472503
0.8143	Intermediate Similarity	NPC192638
0.8125	Intermediate Similarity	NPC41160
0.8116	Intermediate Similarity	NPC23954
0.8116	Intermediate Similarity	NPC164022
0.8116	Intermediate Similarity	NPC477792
0.8088	Intermediate Similarity	NPC210323
0.8082	Intermediate Similarity	NPC24504
0.8082	Intermediate Similarity	NPC209430
0.8082	Intermediate Similarity	NPC476316
0.8082	Intermediate Similarity	NPC30986
0.806	Intermediate Similarity	NPC171225
0.806	Intermediate Similarity	NPC69649
0.806	Intermediate Similarity	NPC68703
0.8056	Intermediate Similarity	NPC91594
0.8033	Intermediate Similarity	NPC84824
0.8033	Intermediate Similarity	NPC67508
0.803	Intermediate Similarity	NPC27243
0.803	Intermediate Similarity	NPC64123
0.803	Intermediate Similarity	NPC476737
0.8028	Intermediate Similarity	NPC3403
0.8028	Intermediate Similarity	NPC200243
0.8028	Intermediate Similarity	NPC70982
0.8028	Intermediate Similarity	NPC178383
0.8028	Intermediate Similarity	NPC212879
0.8028	Intermediate Similarity	NPC104387
0.8028	Intermediate Similarity	NPC32832
0.8028	Intermediate Similarity	NPC231256
0.8028	Intermediate Similarity	NPC240235
0.8028	Intermediate Similarity	NPC141071
0.8028	Intermediate Similarity	NPC230704
0.8028	Intermediate Similarity	NPC471723
0.8028	Intermediate Similarity	NPC257347
0.8	Intermediate Similarity	NPC265485
0.8	Intermediate Similarity	NPC68443
0.8	Intermediate Similarity	NPC471799
0.8	Intermediate Similarity	NPC220939
0.7973	Intermediate Similarity	NPC47149
0.7973	Intermediate Similarity	NPC295131
0.7971	Intermediate Similarity	NPC145498
0.7945	Intermediate Similarity	NPC474216
0.7945	Intermediate Similarity	NPC475
0.7945	Intermediate Similarity	NPC83351
0.7945	Intermediate Similarity	NPC472502
0.7945	Intermediate Similarity	NPC167891
0.7945	Intermediate Similarity	NPC11908
0.7945	Intermediate Similarity	NPC476314
0.7941	Intermediate Similarity	NPC2648
0.7917	Intermediate Similarity	NPC247325
0.7917	Intermediate Similarity	NPC30590
0.7917	Intermediate Similarity	NPC14112
0.7917	Intermediate Similarity	NPC86305
0.7917	Intermediate Similarity	NPC265328
0.7917	Intermediate Similarity	NPC122418
0.7917	Intermediate Similarity	NPC189883
0.7917	Intermediate Similarity	NPC237460
0.7917	Intermediate Similarity	NPC91573
0.7917	Intermediate Similarity	NPC63958
0.7917	Intermediate Similarity	NPC134330
0.7917	Intermediate Similarity	NPC278091
0.7917	Intermediate Similarity	NPC290598
0.7917	Intermediate Similarity	NPC129165
0.7917	Intermediate Similarity	NPC93662
0.7917	Intermediate Similarity	NPC120098
0.7917	Intermediate Similarity	NPC27765
0.7917	Intermediate Similarity	NPC78067
0.7917	Intermediate Similarity	NPC244488
0.7903	Intermediate Similarity	NPC39068
0.7887	Intermediate Similarity	NPC471797
0.7887	Intermediate Similarity	NPC477138
0.7887	Intermediate Similarity	NPC91858
0.7887	Intermediate Similarity	NPC243342
0.7879	Intermediate Similarity	NPC225415
0.7879	Intermediate Similarity	NPC219940
0.7867	Intermediate Similarity	NPC157655
0.7867	Intermediate Similarity	NPC476646
0.7857	Intermediate Similarity	NPC471271
0.7857	Intermediate Similarity	NPC242001
0.7857	Intermediate Similarity	NPC110799
0.7857	Intermediate Similarity	NPC471268
0.7857	Intermediate Similarity	NPC471272
0.7846	Intermediate Similarity	NPC147524
0.7838	Intermediate Similarity	NPC47982
0.7838	Intermediate Similarity	NPC143182
0.7838	Intermediate Similarity	NPC81306
0.7838	Intermediate Similarity	NPC84694
0.7838	Intermediate Similarity	NPC109546
0.7838	Intermediate Similarity	NPC5604
0.7838	Intermediate Similarity	NPC28862
0.7826	Intermediate Similarity	NPC471560
0.7808	Intermediate Similarity	NPC157996
0.7808	Intermediate Similarity	NPC90979
0.7808	Intermediate Similarity	NPC40394
0.7808	Intermediate Similarity	NPC472805
0.7808	Intermediate Similarity	NPC471798
0.7808	Intermediate Similarity	NPC34177
0.7808	Intermediate Similarity	NPC101475
0.7808	Intermediate Similarity	NPC202540
0.7794	Intermediate Similarity	NPC114651
0.7794	Intermediate Similarity	NPC88454
0.7794	Intermediate Similarity	NPC197805
0.7794	Intermediate Similarity	NPC101307
0.7794	Intermediate Similarity	NPC117607
0.7778	Intermediate Similarity	NPC322353
0.7778	Intermediate Similarity	NPC138374
0.7778	Intermediate Similarity	NPC291503
0.7778	Intermediate Similarity	NPC103822
0.7778	Intermediate Similarity	NPC230301
0.7778	Intermediate Similarity	NPC477923
0.7778	Intermediate Similarity	NPC22105
0.7778	Intermediate Similarity	NPC66566
0.7778	Intermediate Similarity	NPC121744
0.7778	Intermediate Similarity	NPC288035
0.7778	Intermediate Similarity	NPC136188
0.7778	Intermediate Similarity	NPC118508
0.7778	Intermediate Similarity	NPC134847

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 NPC68656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2603
0.2-0.3	4067
0.3-0.4	1656
0.4-0.5	358
0.5-0.6	203
0.6-0.7	73
0.7-0.8	17
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
0.7778	Intermediate Similarity	NPD7339	Approved
0.7778	Intermediate Similarity	NPD6942	Approved
0.7671	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7525	Registered
0.7297	Intermediate Similarity	NPD8264	Approved
0.7162	Intermediate Similarity	NPD6926	Approved
0.7162	Intermediate Similarity	NPD6924	Approved
0.7143	Intermediate Similarity	NPD6929	Approved
0.7123	Intermediate Similarity	NPD7152	Approved
0.7123	Intermediate Similarity	NPD7151	Approved
0.7123	Intermediate Similarity	NPD7150	Approved
0.7089	Intermediate Similarity	NPD3667	Approved
0.7083	Intermediate Similarity	NPD6923	Approved
0.7083	Intermediate Similarity	NPD6922	Approved
0.7073	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6930	Phase 2
0.7051	Intermediate Similarity	NPD6931	Approved
0.7037	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD385	Approved
0.7	Intermediate Similarity	NPD384	Approved
0.6986	Remote Similarity	NPD7143	Approved
0.6986	Remote Similarity	NPD7144	Approved
0.6974	Remote Similarity	NPD6933	Approved
0.6951	Remote Similarity	NPD3618	Phase 1
0.6923	Remote Similarity	NPD342	Phase 1
0.6914	Remote Similarity	NPD4786	Approved
0.6892	Remote Similarity	NPD4243	Approved
0.6883	Remote Similarity	NPD6925	Approved
0.6883	Remote Similarity	NPD5776	Phase 2
0.6835	Remote Similarity	NPD7509	Discontinued
0.6835	Remote Similarity	NPD4748	Discontinued
0.6812	Remote Similarity	NPD368	Approved
0.6795	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7145	Approved
0.679	Remote Similarity	NPD6695	Phase 3
0.6711	Remote Similarity	NPD4785	Approved
0.6711	Remote Similarity	NPD4784	Approved
0.6707	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3666	Approved
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD3133	Approved
0.6706	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD6893	Approved
0.6625	Remote Similarity	NPD7332	Phase 2
0.6625	Remote Similarity	NPD7514	Phase 3
0.6623	Remote Similarity	NPD5275	Approved
0.6623	Remote Similarity	NPD4190	Phase 3
0.6622	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4788	Approved
0.6552	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD6079	Approved
0.6543	Remote Similarity	NPD6898	Phase 1
0.6543	Remote Similarity	NPD6902	Approved
0.6533	Remote Similarity	NPD4787	Phase 1
0.6477	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD7750	Discontinued
0.6471	Remote Similarity	NPD7524	Approved
0.6456	Remote Similarity	NPD6932	Approved
0.6447	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7639	Approved
0.6413	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.631	Remote Similarity	NPD3668	Phase 3
0.6304	Remote Similarity	NPD4225	Approved
0.6304	Remote Similarity	NPD7638	Approved
0.6301	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6683	Phase 2
0.6296	Remote Similarity	NPD4195	Approved
0.6282	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5211	Phase 2
0.6264	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5222	Approved
0.6264	Remote Similarity	NPD4697	Phase 3
0.6264	Remote Similarity	NPD5221	Approved
0.6222	Remote Similarity	NPD7748	Approved
0.6203	Remote Similarity	NPD3703	Phase 2
0.6197	Remote Similarity	NPD1145	Discontinued
0.6196	Remote Similarity	NPD5173	Approved
0.6196	Remote Similarity	NPD4755	Approved
0.6184	Remote Similarity	NPD3698	Phase 2
0.618	Remote Similarity	NPD7087	Discontinued
0.6163	Remote Similarity	NPD5279	Phase 3
0.6163	Remote Similarity	NPD4623	Approved
0.6163	Remote Similarity	NPD4519	Discontinued
0.6146	Remote Similarity	NPD5141	Approved
0.6136	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD5290	Discontinued
0.6125	Remote Similarity	NPD6117	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6104	Remote Similarity	NPD4244	Approved
0.6104	Remote Similarity	NPD4245	Approved
0.6087	Remote Similarity	NPD4219	Approved
0.6071	Remote Similarity	NPD4223	Phase 3
0.6071	Remote Similarity	NPD4221	Approved
0.6066	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5286	Approved
0.6064	Remote Similarity	NPD4700	Approved
0.6064	Remote Similarity	NPD4696	Approved
0.6064	Remote Similarity	NPD5285	Approved
0.6049	Remote Similarity	NPD6116	Phase 1
0.6047	Remote Similarity	NPD1696	Phase 3
0.6032	Remote Similarity	NPD386	Approved
0.6032	Remote Similarity	NPD388	Approved
0.6024	Remote Similarity	NPD4695	Discontinued
0.6022	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5223	Approved
0.5976	Remote Similarity	NPD6697	Approved
0.5976	Remote Similarity	NPD3671	Phase 1
0.5976	Remote Similarity	NPD3617	Approved
0.5976	Remote Similarity	NPD6114	Approved
0.5976	Remote Similarity	NPD6118	Approved
0.5976	Remote Similarity	NPD6115	Approved
0.5946	Remote Similarity	NPD371	Approved
0.5938	Remote Similarity	NPD7632	Discontinued
0.5938	Remote Similarity	NPD5226	Approved
0.5938	Remote Similarity	NPD5224	Approved
0.5938	Remote Similarity	NPD5225	Approved
0.5938	Remote Similarity	NPD4633	Approved
0.593	Remote Similarity	NPD4197	Approved
0.5897	Remote Similarity	NPD4789	Approved
0.5889	Remote Similarity	NPD7136	Phase 2
0.5876	Remote Similarity	NPD5175	Approved
0.5876	Remote Similarity	NPD4754	Approved
0.5876	Remote Similarity	NPD5174	Approved
0.5862	Remote Similarity	NPD5329	Approved
0.5844	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD6705	Phase 1
0.5844	Remote Similarity	NPD5360	Phase 3
0.5833	Remote Similarity	NPD4159	Approved
0.5833	Remote Similarity	NPD6928	Phase 2
0.5824	Remote Similarity	NPD7637	Suspended
0.5806	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD4629	Approved
0.5795	Remote Similarity	NPD6409	Approved
0.5795	Remote Similarity	NPD7146	Approved
0.5795	Remote Similarity	NPD7334	Approved
0.5795	Remote Similarity	NPD4689	Approved
0.5795	Remote Similarity	NPD6684	Approved
0.5795	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4688	Approved
0.5795	Remote Similarity	NPD5205	Approved
0.5795	Remote Similarity	NPD4690	Approved
0.5795	Remote Similarity	NPD4138	Approved
0.5795	Remote Similarity	NPD4693	Phase 3
0.5795	Remote Similarity	NPD5330	Approved
0.5795	Remote Similarity	NPD7521	Approved
0.5778	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD5739	Approved
0.5758	Remote Similarity	NPD4768	Approved
0.5758	Remote Similarity	NPD6402	Approved
0.5758	Remote Similarity	NPD7128	Approved
0.5758	Remote Similarity	NPD6675	Approved
0.5758	Remote Similarity	NPD4767	Approved
0.575	Remote Similarity	NPD4732	Discontinued
0.57	Remote Similarity	NPD5697	Approved
0.57	Remote Similarity	NPD5701	Approved
0.5699	Remote Similarity	NPD7900	Approved
0.5699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD6084	Phase 2
0.5684	Remote Similarity	NPD6083	Phase 2
0.5667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4723	Approved
0.5667	Remote Similarity	NPD6903	Approved
0.5667	Remote Similarity	NPD4722	Approved
0.5652	Remote Similarity	NPD6411	Approved
0.5647	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5168	Approved
0.5644	Remote Similarity	NPD6899	Approved
0.5644	Remote Similarity	NPD6011	Approved
0.5644	Remote Similarity	NPD6881	Approved
0.5644	Remote Similarity	NPD4729	Approved
0.5644	Remote Similarity	NPD5128	Approved
0.5644	Remote Similarity	NPD4730	Approved
0.5644	Remote Similarity	NPD7320	Approved
0.5625	Remote Similarity	NPD4758	Discontinued
0.5618	Remote Similarity	NPD4694	Approved
0.5618	Remote Similarity	NPD5280	Approved
0.5618	Remote Similarity	NPD5690	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