NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	254.401
LogP:	3.403
LogD:	3.059
LogS:	-2.421
# 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:	0.666
Synthetic Accessibility Score:	4.222
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:	-4.635
MDCK Permeability:	1.4207145795808174e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.485
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	86.00634765625%
Volume Distribution (VD):	1.951
Pgp-substrate:	11.193532943725586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	11.327
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.688
Skin Sensitization:	0.132
Carcinogencity:	0.48
Eye Corrosion:	0.129
Eye Irritation:	0.272
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC323424

Natural Product ID:	NPC323424
*Common Name:**	(4As,7R)-1,4A-Dimethyl-7-Prop-1-En-2-Yl-3,4,5,6,7,8-Hexahydro-2H-Naphthalen-2-Ol
IUPAC Name:	(4aS,7R)-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	APWLDLGOYJHNIK-ATFAPYMMSA-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,1,5-9H2,2-4H3/t12-,14?,15+/m1/s1
SMILES:	CC(=C)[C@@H]1CC[C@@]2(C(=C(C)C(CC2)O)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2268859
PubChem CID:	5316282
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
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)90945-1]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24704449]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26967731]
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]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22796	Cyperus rotundus	Species	Cyperaceae	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
LD50	1
Others	9

Activity Type	# Activity
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LD50	=	8.78	umol/ml	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	100.0	%	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	96.0	%	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	90.0	%	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	86.7	%	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	70.0	%	PMID[533638]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	mortality	=	50.0	%	PMID[533638]

☑ 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 NPC323424 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	141
0.1-0.2	1598
0.2-0.3	9260
0.3-0.4	16038
0.4-0.5	8526
0.5-0.6	5158
0.6-0.7	1579
0.7-0.8	367
0.8-0.85	22
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96793
0.9062	High Similarity	NPC96484
0.8923	High Similarity	NPC474248
0.8788	High Similarity	NPC34834
0.875	High Similarity	NPC202017
0.8615	High Similarity	NPC171225
0.8615	High Similarity	NPC114651
0.8382	Intermediate Similarity	NPC23954
0.8358	Intermediate Similarity	NPC471560
0.8333	Intermediate Similarity	NPC232247
0.8333	Intermediate Similarity	NPC251666
0.831	Intermediate Similarity	NPC91594
0.8281	Intermediate Similarity	NPC81615
0.8261	Intermediate Similarity	NPC220939
0.8261	Intermediate Similarity	NPC265485
0.8254	Intermediate Similarity	NPC240506
0.8235	Intermediate Similarity	NPC92801
0.8209	Intermediate Similarity	NPC208999
0.8197	Intermediate Similarity	NPC48891
0.8182	Intermediate Similarity	NPC326310
0.8169	Intermediate Similarity	NPC265588
0.8169	Intermediate Similarity	NPC244488
0.8169	Intermediate Similarity	NPC247325
0.8154	Intermediate Similarity	NPC225415
0.8154	Intermediate Similarity	NPC68656
0.8154	Intermediate Similarity	NPC107540
0.8143	Intermediate Similarity	NPC476366
0.8143	Intermediate Similarity	NPC201048
0.8125	Intermediate Similarity	NPC207007
0.8125	Intermediate Similarity	NPC321867
0.8125	Intermediate Similarity	NPC68679
0.8116	Intermediate Similarity	NPC164022
0.8116	Intermediate Similarity	NPC477792
0.8088	Intermediate Similarity	NPC473893
0.8082	Intermediate Similarity	NPC281138
0.806	Intermediate Similarity	NPC68703
0.806	Intermediate Similarity	NPC69649
0.8056	Intermediate Similarity	NPC470758
0.8056	Intermediate Similarity	NPC470711
0.8033	Intermediate Similarity	NPC130209
0.8033	Intermediate Similarity	NPC148216
0.8033	Intermediate Similarity	NPC148163
0.803	Intermediate Similarity	NPC258595
0.803	Intermediate Similarity	NPC287339
0.8028	Intermediate Similarity	NPC32832
0.8028	Intermediate Similarity	NPC133580
0.8	Intermediate Similarity	NPC474155
0.8	Intermediate Similarity	NPC473759
0.8	Intermediate Similarity	NPC182717
0.8	Intermediate Similarity	NPC83200
0.8	Intermediate Similarity	NPC174956
0.7973	Intermediate Similarity	NPC295131
0.7969	Intermediate Similarity	NPC66020
0.7945	Intermediate Similarity	NPC83351
0.7945	Intermediate Similarity	NPC167891
0.7941	Intermediate Similarity	NPC471238
0.7917	Intermediate Similarity	NPC470749
0.7917	Intermediate Similarity	NPC253190
0.791	Intermediate Similarity	NPC476039
0.791	Intermediate Similarity	NPC279434
0.791	Intermediate Similarity	NPC475897
0.791	Intermediate Similarity	NPC286669
0.791	Intermediate Similarity	NPC222366
0.7903	Intermediate Similarity	NPC179024
0.7887	Intermediate Similarity	NPC469534
0.7887	Intermediate Similarity	NPC469593
0.7887	Intermediate Similarity	NPC306727
0.7887	Intermediate Similarity	NPC469533
0.7887	Intermediate Similarity	NPC100334
0.7879	Intermediate Similarity	NPC101128
0.7879	Intermediate Similarity	NPC290367
0.7867	Intermediate Similarity	NPC476646
0.7857	Intermediate Similarity	NPC471271
0.7857	Intermediate Similarity	NPC110799
0.7857	Intermediate Similarity	NPC167706
0.7857	Intermediate Similarity	NPC471268
0.7857	Intermediate Similarity	NPC471272
0.7846	Intermediate Similarity	NPC475251
0.7838	Intermediate Similarity	NPC47982
0.7838	Intermediate Similarity	NPC209430
0.7838	Intermediate Similarity	NPC81306
0.7838	Intermediate Similarity	NPC143182
0.7838	Intermediate Similarity	NPC84694
0.7838	Intermediate Similarity	NPC30986
0.7838	Intermediate Similarity	NPC109546
0.7838	Intermediate Similarity	NPC28862
0.7812	Intermediate Similarity	NPC122239
0.7808	Intermediate Similarity	NPC74995
0.7794	Intermediate Similarity	NPC197805
0.7778	Intermediate Similarity	NPC322353
0.7778	Intermediate Similarity	NPC121744
0.7778	Intermediate Similarity	NPC118508
0.7763	Intermediate Similarity	NPC49964
0.7763	Intermediate Similarity	NPC202389
0.7763	Intermediate Similarity	NPC87489
0.7763	Intermediate Similarity	NPC101462
0.7761	Intermediate Similarity	NPC11555
0.7761	Intermediate Similarity	NPC163678
0.7761	Intermediate Similarity	NPC172613
0.7761	Intermediate Similarity	NPC2728
0.7761	Intermediate Similarity	NPC282619
0.7761	Intermediate Similarity	NPC208198
0.7761	Intermediate Similarity	NPC60837
0.7746	Intermediate Similarity	NPC130665
0.7746	Intermediate Similarity	NPC259049
0.7746	Intermediate Similarity	NPC474743
0.7746	Intermediate Similarity	NPC474140
0.7746	Intermediate Similarity	NPC471799
0.7742	Intermediate Similarity	NPC67508
0.7742	Intermediate Similarity	NPC84824
0.7733	Intermediate Similarity	NPC234193
0.7733	Intermediate Similarity	NPC104120
0.7733	Intermediate Similarity	NPC206062
0.7733	Intermediate Similarity	NPC148685
0.7733	Intermediate Similarity	NPC96362
0.7733	Intermediate Similarity	NPC157895
0.7733	Intermediate Similarity	NPC172013
0.7714	Intermediate Similarity	NPC145498
0.7714	Intermediate Similarity	NPC283316
0.7703	Intermediate Similarity	NPC474216
0.7703	Intermediate Similarity	NPC476314
0.7703	Intermediate Similarity	NPC11908
0.7681	Intermediate Similarity	NPC276616
0.7681	Intermediate Similarity	NPC216460
0.7681	Intermediate Similarity	NPC45264
0.7681	Intermediate Similarity	NPC245795
0.7671	Intermediate Similarity	NPC240604
0.7671	Intermediate Similarity	NPC30590
0.7671	Intermediate Similarity	NPC122418
0.7671	Intermediate Similarity	NPC265328
0.7671	Intermediate Similarity	NPC290598
0.7671	Intermediate Similarity	NPC300324
0.7671	Intermediate Similarity	NPC27765
0.7671	Intermediate Similarity	NPC73875
0.7671	Intermediate Similarity	NPC106364
0.7671	Intermediate Similarity	NPC120098
0.7671	Intermediate Similarity	NPC46160
0.7671	Intermediate Similarity	NPC189883
0.7671	Intermediate Similarity	NPC202642
0.7667	Intermediate Similarity	NPC244038
0.7647	Intermediate Similarity	NPC267027
0.7647	Intermediate Similarity	NPC473929
0.7639	Intermediate Similarity	NPC243342
0.7639	Intermediate Similarity	NPC477138
0.7639	Intermediate Similarity	NPC471797
0.7639	Intermediate Similarity	NPC91858
0.7632	Intermediate Similarity	NPC23852
0.7632	Intermediate Similarity	NPC6663
0.7632	Intermediate Similarity	NPC249423
0.7632	Intermediate Similarity	NPC209620
0.7632	Intermediate Similarity	NPC264245
0.7612	Intermediate Similarity	NPC144650
0.7612	Intermediate Similarity	NPC309300
0.7606	Intermediate Similarity	NPC469343
0.7606	Intermediate Similarity	NPC242992
0.7606	Intermediate Similarity	NPC242001
0.76	Intermediate Similarity	NPC308038
0.76	Intermediate Similarity	NPC242767
0.76	Intermediate Similarity	NPC152061
0.76	Intermediate Similarity	NPC31258
0.7576	Intermediate Similarity	NPC282694
0.7576	Intermediate Similarity	NPC79576
0.7576	Intermediate Similarity	NPC194208
0.7568	Intermediate Similarity	NPC157996
0.7568	Intermediate Similarity	NPC197659
0.7568	Intermediate Similarity	NPC130136
0.7568	Intermediate Similarity	NPC90979
0.7568	Intermediate Similarity	NPC214570
0.7568	Intermediate Similarity	NPC471798
0.7568	Intermediate Similarity	NPC34177
0.7568	Intermediate Similarity	NPC40394
0.7568	Intermediate Similarity	NPC472805
0.7568	Intermediate Similarity	NPC101475
0.7568	Intermediate Similarity	NPC203403
0.7564	Intermediate Similarity	NPC185568
0.7564	Intermediate Similarity	NPC227132
0.7564	Intermediate Similarity	NPC83702
0.7564	Intermediate Similarity	NPC205845
0.7564	Intermediate Similarity	NPC231310
0.7536	Intermediate Similarity	NPC185874
0.7536	Intermediate Similarity	NPC82337
0.7536	Intermediate Similarity	NPC269077
0.7536	Intermediate Similarity	NPC253303
0.7536	Intermediate Similarity	NPC308522
0.7536	Intermediate Similarity	NPC139207
0.7536	Intermediate Similarity	NPC74885
0.7536	Intermediate Similarity	NPC477791
0.7534	Intermediate Similarity	NPC291503
0.7534	Intermediate Similarity	NPC230301
0.7534	Intermediate Similarity	NPC285893
0.7534	Intermediate Similarity	NPC136188
0.7534	Intermediate Similarity	NPC313185
0.7534	Intermediate Similarity	NPC69383
0.7534	Intermediate Similarity	NPC471723
0.7534	Intermediate Similarity	NPC257347
0.7534	Intermediate Similarity	NPC138374
0.7534	Intermediate Similarity	NPC288035
0.7534	Intermediate Similarity	NPC34700
0.7534	Intermediate Similarity	NPC477923
0.7534	Intermediate Similarity	NPC141071

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 NPC323424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	2066
0.2-0.3	4228
0.3-0.4	1948
0.4-0.5	509
0.5-0.6	192
0.6-0.7	53
0.7-0.8	8
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
0.8125	Intermediate Similarity	NPD368	Approved
0.8033	Intermediate Similarity	NPD342	Phase 1
0.7534	Intermediate Similarity	NPD6942	Approved
0.7534	Intermediate Similarity	NPD8264	Approved
0.7534	Intermediate Similarity	NPD7339	Approved
0.7432	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7645	Phase 2
0.7344	Intermediate Similarity	NPD4219	Approved
0.7324	Intermediate Similarity	NPD6922	Approved
0.7324	Intermediate Similarity	NPD6923	Approved
0.7237	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7143	Approved
0.7222	Intermediate Similarity	NPD7144	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
0.7105	Intermediate Similarity	NPD5776	Phase 2
0.7105	Intermediate Similarity	NPD6925	Approved
0.7073	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6930	Phase 2
0.7051	Intermediate Similarity	NPD6931	Approved
0.7051	Intermediate Similarity	NPD7514	Phase 3
0.7051	Intermediate Similarity	NPD7332	Phase 2
0.7051	Intermediate Similarity	NPD7525	Registered
0.7013	Intermediate Similarity	NPD7145	Approved
0.6974	Remote Similarity	NPD6933	Approved
0.6962	Remote Similarity	NPD6902	Approved
0.6892	Remote Similarity	NPD4243	Approved
0.6875	Remote Similarity	NPD3667	Approved
0.679	Remote Similarity	NPD6695	Phase 3
0.675	Remote Similarity	NPD6898	Phase 1
0.6747	Remote Similarity	NPD3618	Phase 1
0.6711	Remote Similarity	NPD4785	Approved
0.6711	Remote Similarity	NPD4784	Approved
0.6707	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD4786	Approved
0.6707	Remote Similarity	NPD3133	Approved
0.6707	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6627	Remote Similarity	NPD6893	Approved
0.6625	Remote Similarity	NPD4748	Discontinued
0.6625	Remote Similarity	NPD7509	Discontinued
0.6623	Remote Similarity	NPD5275	Approved
0.6623	Remote Similarity	NPD4190	Phase 3
0.6579	Remote Similarity	NPD4732	Discontinued
0.6512	Remote Similarity	NPD5328	Approved
0.65	Remote Similarity	NPD6683	Phase 2
0.6471	Remote Similarity	NPD7750	Discontinued
0.6471	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD385	Approved
0.6452	Remote Similarity	NPD384	Approved
0.6364	Remote Similarity	NPD7515	Phase 2
0.6364	Remote Similarity	NPD6079	Approved
0.6353	Remote Similarity	NPD4623	Approved
0.6353	Remote Similarity	NPD4519	Discontinued
0.6353	Remote Similarity	NPD5279	Phase 3
0.631	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4195	Approved
0.6292	Remote Similarity	NPD4202	Approved
0.6237	Remote Similarity	NPD7640	Approved
0.6237	Remote Similarity	NPD7639	Approved
0.6235	Remote Similarity	NPD1696	Phase 3
0.618	Remote Similarity	NPD7087	Discontinued
0.618	Remote Similarity	NPD7637	Suspended
0.6173	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD4225	Approved
0.6118	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD4194	Approved
0.6111	Remote Similarity	NPD4192	Approved
0.6111	Remote Similarity	NPD4191	Approved
0.6111	Remote Similarity	NPD4193	Approved
0.6105	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD5222	Approved
0.6087	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4697	Phase 3
0.6087	Remote Similarity	NPD5221	Approved
0.6071	Remote Similarity	NPD4221	Approved
0.6071	Remote Similarity	NPD4223	Phase 3
0.6067	Remote Similarity	NPD7136	Phase 2
0.6047	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD1694	Approved
0.6044	Remote Similarity	NPD7748	Approved
0.6032	Remote Similarity	NPD4265	Approved
0.6024	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4695	Discontinued
0.6022	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD4755	Approved
0.5979	Remote Similarity	NPD5141	Approved
0.5976	Remote Similarity	NPD3617	Approved
0.5974	Remote Similarity	NPD791	Approved
0.5974	Remote Similarity	NPD15	Approved
0.5957	Remote Similarity	NPD5290	Discontinued
0.5955	Remote Similarity	NPD6051	Approved
0.5934	Remote Similarity	NPD5779	Approved
0.5934	Remote Similarity	NPD6399	Phase 3
0.5934	Remote Similarity	NPD5778	Approved
0.593	Remote Similarity	NPD4197	Approved
0.5895	Remote Similarity	NPD4696	Approved
0.5895	Remote Similarity	NPD4700	Approved
0.5895	Remote Similarity	NPD5285	Approved
0.5895	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD5329	Approved
0.5851	Remote Similarity	NPD7902	Approved
0.5833	Remote Similarity	NPD4822	Approved
0.5833	Remote Similarity	NPD4819	Approved
0.5833	Remote Similarity	NPD4820	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5833	Remote Similarity	NPD4821	Approved
0.5833	Remote Similarity	NPD4159	Approved
0.5824	Remote Similarity	NPD6411	Approved
0.5814	Remote Similarity	NPD5332	Approved
0.5814	Remote Similarity	NPD7154	Phase 3
0.5814	Remote Similarity	NPD5362	Discontinued
0.5814	Remote Similarity	NPD5331	Approved
0.5814	Remote Similarity	NPD4788	Approved
0.5806	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD4629	Approved
0.5802	Remote Similarity	NPD8039	Approved
0.5795	Remote Similarity	NPD6409	Approved
0.5795	Remote Similarity	NPD5690	Phase 2
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	NPD5205	Approved
0.5795	Remote Similarity	NPD4690	Approved
0.5795	Remote Similarity	NPD4138	Approved
0.5795	Remote Similarity	NPD4694	Approved
0.5795	Remote Similarity	NPD4693	Phase 3
0.5795	Remote Similarity	NPD5330	Approved
0.5795	Remote Similarity	NPD4688	Approved
0.5795	Remote Similarity	NPD7521	Approved
0.5795	Remote Similarity	NPD5280	Approved
0.5789	Remote Similarity	NPD7331	Phase 2
0.5783	Remote Similarity	NPD4271	Approved
0.5783	Remote Similarity	NPD4268	Approved
0.5773	Remote Similarity	NPD5224	Approved
0.5773	Remote Similarity	NPD5225	Approved
0.5773	Remote Similarity	NPD4633	Approved
0.5773	Remote Similarity	NPD7632	Discontinued
0.5773	Remote Similarity	NPD5226	Approved
0.5765	Remote Similarity	NPD4790	Discontinued
0.5765	Remote Similarity	NPD4139	Approved
0.5765	Remote Similarity	NPD4692	Approved
0.5753	Remote Similarity	NPD1145	Discontinued
0.5733	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD1346	Approved
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5698	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD4269	Approved
0.5698	Remote Similarity	NPD4270	Approved
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
0.5658	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD7341	Phase 2
0.5647	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5695	Phase 3
0.5604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD6101	Approved
0.56	Remote Similarity	NPD4768	Approved
0.56	Remote Similarity	NPD6640	Phase 3
0.56	Remote Similarity	NPD7128	Approved
0.56	Remote Similarity	NPD4767	Approved
0.56	Remote Similarity	NPD5739	Approved
0.56	Remote Similarity	NPD6402	Approved
0.56	Remote Similarity	NPD6675	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