NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.732
LogD:	3.205
LogS:	-2.528
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	4.348
Fsp3:	0.867
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:	-4.554
MDCK Permeability:	1.791251816030126e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.469
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.251

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	61.96894836425781%
Volume Distribution (VD):	0.818
Pgp-substrate:	37.53302764892578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.331
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	13.565
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.055
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.775
Maximum Recommended Daily Dose:	0.053
Skin Sensitization:	0.162
Carcinogencity:	0.122
Eye Corrosion:	0.054
Eye Irritation:	0.134
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC300442

Natural Product ID:	NPC300442
*Common Name:**	Octahydro-4-Hydroxy-3Alpha-Methyl-7-Methylene-Alpha-(1-Methylethyl)-1H-Indene-1-Methanol
IUPAC Name:	(1R,3aS,4S,7aR)-1-[(1S)-1-hydroxy-2-methylpropyl]-3a-methyl-7-methylidene-2,3,4,5,6,7a-hexahydro-1H-inden-4-ol
Synonyms:
Standard InCHIKey:	OZBVMKPZPKMEGY-CAEXGNQWSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-9(2)14(17)11-7-8-15(4)12(16)6-5-10(3)13(11)15/h9,11-14,16-17H,3,5-8H2,1-2,4H3/t11-,12+,13+,14+,15-/m1/s1
SMILES:	CC(C)[C@@H]([C@@H]1CC[C@]2(C)[C@H](CCC(=C)[C@@H]12)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464961
PubChem CID:	21629614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762792]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	Whole plants	Mountain Emei, Sichuan Province, China	2008-OCT	PMID[21561060]
NPO29956	Sanicula lamelligera	Species	Apiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21561060]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22051	Litsea verticillata	Species	Lauraceae	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
EC50	1
IC50	6
Others	3

Activity Type	# Activity
Cell Line	7
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	64400.0	nM	PMID[512068]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	64400.0	nM	PMID[512068]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	64400.0	nM	PMID[512068]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	64400.0	nM	PMID[512068]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	64400.0	nM	PMID[512068]
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	397900.0	nM	PMID[512068]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	64400.0	nM	PMID[512068]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	39.0	%	PMID[512067]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	2.4	n.a.	PMID[512068]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	166800.0	nM	PMID[512068]

☑ 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 NPC300442 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	130
0.1-0.2	1978
0.2-0.3	11902
0.3-0.4	13407
0.4-0.5	6499
0.5-0.6	6129
0.6-0.7	2187
0.7-0.8	442
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9508	High Similarity	NPC219940
0.8551	High Similarity	NPC308440
0.8551	High Similarity	NPC472503
0.8485	Intermediate Similarity	NPC269077
0.8485	Intermediate Similarity	NPC253303
0.8451	Intermediate Similarity	NPC202540
0.8333	Intermediate Similarity	NPC477817
0.8333	Intermediate Similarity	NPC477819
0.8333	Intermediate Similarity	NPC31828
0.8308	Intermediate Similarity	NPC101128
0.8308	Intermediate Similarity	NPC144650
0.8281	Intermediate Similarity	NPC147524
0.8261	Intermediate Similarity	NPC111234
0.8219	Intermediate Similarity	NPC116119
0.8219	Intermediate Similarity	NPC472742
0.8219	Intermediate Similarity	NPC475727
0.8219	Intermediate Similarity	NPC80297
0.8209	Intermediate Similarity	NPC74885
0.8209	Intermediate Similarity	NPC308522
0.8182	Intermediate Similarity	NPC11555
0.8182	Intermediate Similarity	NPC208198
0.8182	Intermediate Similarity	NPC172613
0.8182	Intermediate Similarity	NPC282619
0.8182	Intermediate Similarity	NPC2728
0.8182	Intermediate Similarity	NPC60837
0.8169	Intermediate Similarity	NPC212879
0.8169	Intermediate Similarity	NPC185536
0.8169	Intermediate Similarity	NPC231256
0.8169	Intermediate Similarity	NPC230704
0.8169	Intermediate Similarity	NPC103822
0.8169	Intermediate Similarity	NPC240235
0.8169	Intermediate Similarity	NPC104387
0.8169	Intermediate Similarity	NPC70982
0.8169	Intermediate Similarity	NPC178383
0.8169	Intermediate Similarity	NPC3403
0.8116	Intermediate Similarity	NPC283316
0.8116	Intermediate Similarity	NPC45296
0.8108	Intermediate Similarity	NPC78545
0.8108	Intermediate Similarity	NPC475679
0.8108	Intermediate Similarity	NPC71535
0.8088	Intermediate Similarity	NPC245795
0.8082	Intermediate Similarity	NPC472500
0.8082	Intermediate Similarity	NPC472502
0.8082	Intermediate Similarity	NPC472499
0.8082	Intermediate Similarity	NPC475
0.8056	Intermediate Similarity	NPC93662
0.8056	Intermediate Similarity	NPC14112
0.8056	Intermediate Similarity	NPC278091
0.8056	Intermediate Similarity	NPC73875
0.8056	Intermediate Similarity	NPC91573
0.8056	Intermediate Similarity	NPC78067
0.8056	Intermediate Similarity	NPC86305
0.803	Intermediate Similarity	NPC225415
0.8028	Intermediate Similarity	NPC49168
0.8028	Intermediate Similarity	NPC254509
0.8028	Intermediate Similarity	NPC192638
0.8028	Intermediate Similarity	NPC145552
0.8028	Intermediate Similarity	NPC196358
0.8028	Intermediate Similarity	NPC5046
0.8028	Intermediate Similarity	NPC25511
0.8028	Intermediate Similarity	NPC62657
0.8	Intermediate Similarity	NPC469343
0.7973	Intermediate Similarity	NPC24504
0.7973	Intermediate Similarity	NPC476316
0.7945	Intermediate Similarity	NPC214570
0.7945	Intermediate Similarity	NPC31037
0.7945	Intermediate Similarity	NPC119355
0.7945	Intermediate Similarity	NPC257191
0.7945	Intermediate Similarity	NPC248830
0.7945	Intermediate Similarity	NPC331618
0.7945	Intermediate Similarity	NPC212241
0.7941	Intermediate Similarity	NPC185874
0.7941	Intermediate Similarity	NPC139207
0.7917	Intermediate Similarity	NPC322353
0.7917	Intermediate Similarity	NPC200243
0.7917	Intermediate Similarity	NPC118508
0.7917	Intermediate Similarity	NPC121744
0.791	Intermediate Similarity	NPC258595
0.7903	Intermediate Similarity	NPC84824
0.7903	Intermediate Similarity	NPC67508
0.7887	Intermediate Similarity	NPC474140
0.7887	Intermediate Similarity	NPC95165
0.7887	Intermediate Similarity	NPC195489
0.7867	Intermediate Similarity	NPC47149
0.7838	Intermediate Similarity	NPC244385
0.7838	Intermediate Similarity	NPC138621
0.7838	Intermediate Similarity	NPC102708
0.7838	Intermediate Similarity	NPC285761
0.7838	Intermediate Similarity	NPC472342
0.7838	Intermediate Similarity	NPC275910
0.7838	Intermediate Similarity	NPC167037
0.7838	Intermediate Similarity	NPC6978
0.7838	Intermediate Similarity	NPC42853
0.7838	Intermediate Similarity	NPC301707
0.7838	Intermediate Similarity	NPC87604
0.7826	Intermediate Similarity	NPC266578
0.7826	Intermediate Similarity	NPC244790
0.7808	Intermediate Similarity	NPC189883
0.7808	Intermediate Similarity	NPC46160
0.7808	Intermediate Similarity	NPC202642
0.7808	Intermediate Similarity	NPC237460
0.7794	Intermediate Similarity	NPC473929
0.7792	Intermediate Similarity	NPC110778
0.7792	Intermediate Similarity	NPC85095
0.7792	Intermediate Similarity	NPC232023
0.7792	Intermediate Similarity	NPC216420
0.7792	Intermediate Similarity	NPC113978
0.7792	Intermediate Similarity	NPC470929
0.7792	Intermediate Similarity	NPC211135
0.7792	Intermediate Similarity	NPC477818
0.7778	Intermediate Similarity	NPC199316
0.7778	Intermediate Similarity	NPC27395
0.7778	Intermediate Similarity	NPC102313
0.7778	Intermediate Similarity	NPC329090
0.7763	Intermediate Similarity	NPC470383
0.7761	Intermediate Similarity	NPC68656
0.7733	Intermediate Similarity	NPC472463
0.7733	Intermediate Similarity	NPC49599
0.7733	Intermediate Similarity	NPC273410
0.7733	Intermediate Similarity	NPC80530
0.7733	Intermediate Similarity	NPC49627
0.7733	Intermediate Similarity	NPC1319
0.7714	Intermediate Similarity	NPC234511
0.7703	Intermediate Similarity	NPC307336
0.7703	Intermediate Similarity	NPC138502
0.7703	Intermediate Similarity	NPC260301
0.7692	Intermediate Similarity	NPC86238
0.7692	Intermediate Similarity	NPC255882
0.7692	Intermediate Similarity	NPC124172
0.7692	Intermediate Similarity	NPC209802
0.7692	Intermediate Similarity	NPC242016
0.7671	Intermediate Similarity	NPC319090
0.7671	Intermediate Similarity	NPC328104
0.7671	Intermediate Similarity	NPC257347
0.7671	Intermediate Similarity	NPC141071
0.7671	Intermediate Similarity	NPC313185
0.7671	Intermediate Similarity	NPC471723
0.7662	Intermediate Similarity	NPC472504
0.7662	Intermediate Similarity	NPC248886
0.7647	Intermediate Similarity	NPC238352
0.7647	Intermediate Similarity	NPC27243
0.7647	Intermediate Similarity	NPC477009
0.7647	Intermediate Similarity	NPC476737
0.7639	Intermediate Similarity	NPC234527
0.7639	Intermediate Similarity	NPC201373
0.7639	Intermediate Similarity	NPC472506
0.7639	Intermediate Similarity	NPC14352
0.7632	Intermediate Similarity	NPC236237
0.7632	Intermediate Similarity	NPC102253
0.7632	Intermediate Similarity	NPC322313
0.7632	Intermediate Similarity	NPC13554
0.7632	Intermediate Similarity	NPC324772
0.7632	Intermediate Similarity	NPC236112
0.7632	Intermediate Similarity	NPC26117
0.7612	Intermediate Similarity	NPC249078
0.7612	Intermediate Similarity	NPC236099
0.7612	Intermediate Similarity	NPC209686
0.7606	Intermediate Similarity	NPC92801
0.76	Intermediate Similarity	NPC65897
0.76	Intermediate Similarity	NPC205455
0.76	Intermediate Similarity	NPC472501
0.76	Intermediate Similarity	NPC186191
0.76	Intermediate Similarity	NPC302041
0.76	Intermediate Similarity	NPC85346
0.7571	Intermediate Similarity	NPC276616
0.7571	Intermediate Similarity	NPC167527
0.7571	Intermediate Similarity	NPC160209
0.7568	Intermediate Similarity	NPC470362
0.7568	Intermediate Similarity	NPC129165
0.7568	Intermediate Similarity	NPC134330
0.7568	Intermediate Similarity	NPC63958
0.7568	Intermediate Similarity	NPC321016
0.7568	Intermediate Similarity	NPC321381
0.7568	Intermediate Similarity	NPC107059
0.7568	Intermediate Similarity	NPC300324
0.7568	Intermediate Similarity	NPC38141
0.7568	Intermediate Similarity	NPC240604
0.7568	Intermediate Similarity	NPC315261
0.7564	Intermediate Similarity	NPC141941
0.7564	Intermediate Similarity	NPC193870
0.7538	Intermediate Similarity	NPC474769
0.7538	Intermediate Similarity	NPC189290
0.7536	Intermediate Similarity	NPC475897
0.7534	Intermediate Similarity	NPC306727
0.7534	Intermediate Similarity	NPC469534
0.7534	Intermediate Similarity	NPC476736
0.7534	Intermediate Similarity	NPC309178
0.7534	Intermediate Similarity	NPC469533
0.7534	Intermediate Similarity	NPC469593
0.7532	Intermediate Similarity	NPC23852
0.7532	Intermediate Similarity	NPC209620
0.7532	Intermediate Similarity	NPC320525
0.7532	Intermediate Similarity	NPC474531
0.75	Intermediate Similarity	NPC30986
0.75	Intermediate Similarity	NPC6391
0.75	Intermediate Similarity	NPC41886
0.75	Intermediate Similarity	NPC121981
0.75	Intermediate Similarity	NPC309300
0.75	Intermediate Similarity	NPC164045
0.75	Intermediate Similarity	NPC24443

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 NPC300442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	2684
0.2-0.3	4246
0.3-0.4	1453
0.4-0.5	293
0.5-0.6	258
0.6-0.7	66
0.7-0.8	26
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	NPD6924	Approved
0.7778	Intermediate Similarity	NPD6926	Approved
0.7733	Intermediate Similarity	NPD6929	Approved
0.7632	Intermediate Similarity	NPD6931	Approved
0.7632	Intermediate Similarity	NPD6930	Phase 2
0.7632	Intermediate Similarity	NPD7525	Registered
0.7568	Intermediate Similarity	NPD6933	Approved
0.7467	Intermediate Similarity	NPD6932	Approved
0.7467	Intermediate Similarity	NPD5776	Phase 2
0.7467	Intermediate Similarity	NPD6925	Approved
0.7465	Intermediate Similarity	NPD6922	Approved
0.7465	Intermediate Similarity	NPD6923	Approved
0.7432	Intermediate Similarity	NPD6942	Approved
0.7432	Intermediate Similarity	NPD7339	Approved
0.7368	Intermediate Similarity	NPD7145	Approved
0.7361	Intermediate Similarity	NPD7144	Approved
0.7361	Intermediate Similarity	NPD7143	Approved
0.7342	Intermediate Similarity	NPD6695	Phase 3
0.7333	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6683	Phase 2
0.726	Intermediate Similarity	NPD7150	Approved
0.726	Intermediate Similarity	NPD7151	Approved
0.726	Intermediate Similarity	NPD7152	Approved
0.725	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7514	Phase 3
0.7179	Intermediate Similarity	NPD7509	Discontinued
0.716	Intermediate Similarity	NPD6893	Approved
0.716	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6902	Approved
0.6988	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7750	Discontinued
0.6988	Remote Similarity	NPD7524	Approved
0.6962	Remote Similarity	NPD4748	Discontinued
0.6962	Remote Similarity	NPD7332	Phase 2
0.6885	Remote Similarity	NPD384	Approved
0.6885	Remote Similarity	NPD385	Approved
0.6875	Remote Similarity	NPD6898	Phase 1
0.6867	Remote Similarity	NPD3618	Phase 1
0.6835	Remote Similarity	NPD7645	Phase 2
0.6829	Remote Similarity	NPD4786	Approved
0.6824	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD4243	Approved
0.679	Remote Similarity	NPD3667	Approved
0.6757	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD6079	Approved
0.6627	Remote Similarity	NPD3665	Phase 1
0.6627	Remote Similarity	NPD3133	Approved
0.6627	Remote Similarity	NPD3666	Approved
0.6623	Remote Similarity	NPD4784	Approved
0.6623	Remote Similarity	NPD4785	Approved
0.6591	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD5275	Approved
0.6538	Remote Similarity	NPD3703	Phase 2
0.6538	Remote Similarity	NPD4190	Phase 3
0.65	Remote Similarity	NPD6697	Approved
0.65	Remote Similarity	NPD6114	Approved
0.65	Remote Similarity	NPD6115	Approved
0.65	Remote Similarity	NPD6118	Approved
0.6479	Remote Similarity	NPD368	Approved
0.6477	Remote Similarity	NPD8034	Phase 2
0.6477	Remote Similarity	NPD8035	Phase 2
0.6447	Remote Similarity	NPD4787	Phase 1
0.6438	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4195	Approved
0.6413	Remote Similarity	NPD7638	Approved
0.6374	Remote Similarity	NPD4697	Phase 3
0.6374	Remote Similarity	NPD5222	Approved
0.6374	Remote Similarity	NPD5221	Approved
0.6374	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7639	Approved
0.6344	Remote Similarity	NPD7640	Approved
0.6329	Remote Similarity	NPD8264	Approved
0.6316	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5173	Approved
0.6304	Remote Similarity	NPD4755	Approved
0.6292	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD6117	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6203	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4223	Phase 3
0.619	Remote Similarity	NPD388	Approved
0.619	Remote Similarity	NPD386	Approved
0.619	Remote Similarity	NPD4221	Approved
0.618	Remote Similarity	NPD7136	Phase 2
0.6173	Remote Similarity	NPD6116	Phase 1
0.617	Remote Similarity	NPD4700	Approved
0.617	Remote Similarity	NPD5286	Approved
0.617	Remote Similarity	NPD5285	Approved
0.617	Remote Similarity	NPD4696	Approved
0.6145	Remote Similarity	NPD6928	Phase 2
0.6111	Remote Similarity	NPD1145	Discontinued
0.6105	Remote Similarity	NPD5223	Approved
0.6104	Remote Similarity	NPD3698	Phase 2
0.6098	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD342	Phase 1
0.6081	Remote Similarity	NPD371	Approved
0.6064	Remote Similarity	NPD5290	Discontinued
0.6047	Remote Similarity	NPD3668	Phase 3
0.6047	Remote Similarity	NPD4197	Approved
0.6044	Remote Similarity	NPD6399	Phase 3
0.6042	Remote Similarity	NPD5211	Phase 2
0.6042	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD5224	Approved
0.6042	Remote Similarity	NPD5225	Approved
0.6042	Remote Similarity	NPD4633	Approved
0.6026	Remote Similarity	NPD4789	Approved
0.6026	Remote Similarity	NPD4245	Approved
0.6026	Remote Similarity	NPD4244	Approved
0.5979	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD4754	Approved
0.5979	Remote Similarity	NPD5174	Approved
0.5977	Remote Similarity	NPD5329	Approved
0.5974	Remote Similarity	NPD6705	Phase 1
0.5941	Remote Similarity	NPD4634	Approved
0.5934	Remote Similarity	NPD7515	Phase 2
0.5918	Remote Similarity	NPD5141	Approved
0.5914	Remote Similarity	NPD5210	Approved
0.5914	Remote Similarity	NPD4629	Approved
0.5909	Remote Similarity	NPD4138	Approved
0.5909	Remote Similarity	NPD4694	Approved
0.5909	Remote Similarity	NPD5205	Approved
0.5909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4693	Phase 3
0.5909	Remote Similarity	NPD4689	Approved
0.5909	Remote Similarity	NPD4688	Approved
0.5909	Remote Similarity	NPD4690	Approved
0.5909	Remote Similarity	NPD5280	Approved
0.5909	Remote Similarity	NPD5690	Phase 2
0.5904	Remote Similarity	NPD3617	Approved
0.5882	Remote Similarity	NPD4692	Approved
0.5882	Remote Similarity	NPD4139	Approved
0.5876	Remote Similarity	NPD7632	Discontinued
0.5875	Remote Similarity	NPD4732	Discontinued
0.5859	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD4767	Approved
0.5859	Remote Similarity	NPD6402	Approved
0.5859	Remote Similarity	NPD7128	Approved
0.5859	Remote Similarity	NPD6675	Approved
0.5859	Remote Similarity	NPD4768	Approved
0.58	Remote Similarity	NPD5697	Approved
0.58	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5778	Remote Similarity	NPD4722	Approved
0.5778	Remote Similarity	NPD4723	Approved
0.5769	Remote Similarity	NPD5360	Phase 3
0.5769	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4632	Approved
0.5747	Remote Similarity	NPD5362	Discontinued
0.5747	Remote Similarity	NPD5331	Approved
0.5747	Remote Similarity	NPD5332	Approved
0.5745	Remote Similarity	NPD5695	Phase 3
0.5743	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD4729	Approved
0.5743	Remote Similarity	NPD5128	Approved
0.5743	Remote Similarity	NPD7320	Approved
0.5743	Remote Similarity	NPD4730	Approved
0.5743	Remote Similarity	NPD6881	Approved
0.5743	Remote Similarity	NPD6899	Approved
0.5743	Remote Similarity	NPD5168	Approved
0.573	Remote Similarity	NPD7521	Approved
0.573	Remote Similarity	NPD7146	Approved
0.573	Remote Similarity	NPD7334	Approved
0.573	Remote Similarity	NPD6684	Approved
0.573	Remote Similarity	NPD6409	Approved
0.573	Remote Similarity	NPD5330	Approved
0.5729	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD3671	Phase 1
0.5698	Remote Similarity	NPD4790	Discontinued
0.5686	Remote Similarity	NPD6373	Approved
0.5686	Remote Similarity	NPD6013	Approved
0.5686	Remote Similarity	NPD6012	Approved
0.5686	Remote Similarity	NPD6372	Approved
0.5686	Remote Similarity	NPD6014	Approved
0.5672	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD1346	Approved
0.5652	Remote Similarity	NPD6700	Approved
0.5652	Remote Similarity	NPD4096	Approved
0.5652	Remote Similarity	NPD3168	Discontinued
0.5652	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD6412	Phase 2
0.5638	Remote Similarity	NPD7748	Approved
0.5631	Remote Similarity	NPD7102	Approved
0.5631	Remote Similarity	NPD5248	Approved
0.5631	Remote Similarity	NPD6883	Approved
0.5631	Remote Similarity	NPD7290	Approved
0.5631	Remote Similarity	NPD5135	Approved
0.5631	Remote Similarity	NPD5169	Approved
0.5631	Remote Similarity	NPD5251	Approved
0.5631	Remote Similarity	NPD5250	Approved
0.5631	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5247	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