NPASS Compound

Structure

NPC68443 OpenBabel07101718252D 22 23 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 6 0 0 0 17 20 1 1 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	2.872
LogD:	2.977
LogS:	-3.95
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	4.74
Fsp3:	0.7
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:	-4.757
MDCK Permeability:	1.7042377294274047e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.439
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.767
Plasma Protein Binding (PPB):	67.76668548583984%
Volume Distribution (VD):	1.464
Pgp-substrate:	24.65713882446289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.218
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.428
CYP3A4-inhibitor:	0.59
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	7.837
Half-life (T1/2):	0.648

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.217
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.673
Carcinogencity:	0.227
Eye Corrosion:	0.398
Eye Irritation:	0.909
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC68443

Natural Product ID:	NPC68443
*Common Name:**	Labda-8(17),12E,14-Triene-2R,18-Diol
IUPAC Name:	(2R,4R,4aR,8S,8aR)-4-(hydroxymethyl)-4,8a-dimethyl-7-methylidene-8-[(2E)-3-methylpenta-2,4-dienyl]-2,3,4a,5,6,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	SWIIQEZMLWUBRB-CWNDDPNYSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-14(2)7-9-17-15(3)8-10-18-19(4,13-21)11-16(22)12-20(17,18)5/h6-7,16-18,21-22H,1,3,8-13H2,2,4-5H3/b14-7+/t16-,17-,18-,19-,20+/m0/s1
SMILES:	C=C/C(=C/C[C@H]1C(=C)CC[C@H]2[C@@](C)(C[C@@H](C[C@]12C)O)CO)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL220528
PubChem CID:	16109841
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO23470	Orthosiphon labiatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256988]
NPO32827	salvia africana-lutea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256988]
NPO23470	Orthosiphon labiatus	Species	Lamiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	82000.0	nM	PMID[553349]

☑ 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 NPC68443 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	170
0.1-0.2	1120
0.2-0.3	5338
0.3-0.4	15599
0.4-0.5	10022
0.5-0.6	6433
0.6-0.7	3009
0.7-0.8	837
0.8-0.85	114
0.85-0.9	42
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC106432
0.9155	High Similarity	NPC291503
0.9104	High Similarity	NPC149680
0.9014	High Similarity	NPC477138
0.9014	High Similarity	NPC91858
0.9014	High Similarity	NPC243342
0.9	High Similarity	NPC242001
0.9	High Similarity	NPC167706
0.8873	High Similarity	NPC471799
0.8873	High Similarity	NPC182717
0.8857	High Similarity	NPC145498
0.8767	High Similarity	NPC274079
0.8767	High Similarity	NPC477925
0.875	High Similarity	NPC471797
0.875	High Similarity	NPC306727
0.8714	High Similarity	NPC476431
0.8714	High Similarity	NPC9942
0.8649	High Similarity	NPC471798
0.863	High Similarity	NPC477923
0.863	High Similarity	NPC66566
0.863	High Similarity	NPC328104
0.863	High Similarity	NPC319090
0.8592	High Similarity	NPC92801
0.8571	High Similarity	NPC208999
0.8571	High Similarity	NPC471238
0.8571	High Similarity	NPC32055
0.8553	High Similarity	NPC96362
0.8553	High Similarity	NPC287749
0.8533	High Similarity	NPC18603
0.8533	High Similarity	NPC300499
0.8533	High Similarity	NPC6978
0.8533	High Similarity	NPC244385
0.8533	High Similarity	NPC307965
0.8533	High Similarity	NPC76931
0.8533	High Similarity	NPC167037
0.8533	High Similarity	NPC72507
0.8533	High Similarity	NPC138621
0.8529	High Similarity	NPC225415
0.8514	High Similarity	NPC134330
0.8514	High Similarity	NPC129165
0.8514	High Similarity	NPC265588
0.8514	High Similarity	NPC253190
0.8514	High Similarity	NPC63958
0.8493	Intermediate Similarity	NPC201048
0.8493	Intermediate Similarity	NPC476366
0.8493	Intermediate Similarity	NPC27395
0.8493	Intermediate Similarity	NPC100334
0.8493	Intermediate Similarity	NPC329090
0.8472	Intermediate Similarity	NPC110799
0.8472	Intermediate Similarity	NPC164022
0.8462	Intermediate Similarity	NPC52108
0.8462	Intermediate Similarity	NPC474789
0.8462	Intermediate Similarity	NPC312480
0.8462	Intermediate Similarity	NPC82538
0.8462	Intermediate Similarity	NPC237795
0.8442	Intermediate Similarity	NPC476646
0.8429	Intermediate Similarity	NPC69649
0.8429	Intermediate Similarity	NPC68703
0.8429	Intermediate Similarity	NPC197805
0.8421	Intermediate Similarity	NPC80530
0.8421	Intermediate Similarity	NPC273410
0.84	Intermediate Similarity	NPC101475
0.84	Intermediate Similarity	NPC90979
0.84	Intermediate Similarity	NPC157996
0.84	Intermediate Similarity	NPC470758
0.84	Intermediate Similarity	NPC477924
0.84	Intermediate Similarity	NPC130136
0.84	Intermediate Similarity	NPC91594
0.84	Intermediate Similarity	NPC34177
0.84	Intermediate Similarity	NPC470711
0.84	Intermediate Similarity	NPC40394
0.84	Intermediate Similarity	NPC472805
0.8378	Intermediate Similarity	NPC257347
0.8378	Intermediate Similarity	NPC171148
0.8378	Intermediate Similarity	NPC69383
0.8378	Intermediate Similarity	NPC313179
0.8378	Intermediate Similarity	NPC141071
0.8378	Intermediate Similarity	NPC471723
0.8356	Intermediate Similarity	NPC474140
0.8354	Intermediate Similarity	NPC474493
0.8333	Intermediate Similarity	NPC49422
0.8333	Intermediate Similarity	NPC9161
0.8333	Intermediate Similarity	NPC34834
0.8312	Intermediate Similarity	NPC236237
0.8312	Intermediate Similarity	NPC102253
0.8312	Intermediate Similarity	NPC322313
0.831	Intermediate Similarity	NPC216460
0.8289	Intermediate Similarity	NPC285761
0.8289	Intermediate Similarity	NPC205455
0.8289	Intermediate Similarity	NPC167891
0.8289	Intermediate Similarity	NPC99168
0.8289	Intermediate Similarity	NPC253807
0.8289	Intermediate Similarity	NPC11908
0.8289	Intermediate Similarity	NPC470396
0.8289	Intermediate Similarity	NPC22955
0.8289	Intermediate Similarity	NPC196753
0.8289	Intermediate Similarity	NPC230295
0.8289	Intermediate Similarity	NPC476314
0.8289	Intermediate Similarity	NPC83351
0.8289	Intermediate Similarity	NPC98386
0.8289	Intermediate Similarity	NPC474989
0.8289	Intermediate Similarity	NPC158662
0.8289	Intermediate Similarity	NPC186191
0.8289	Intermediate Similarity	NPC318136
0.8286	Intermediate Similarity	NPC286669
0.8286	Intermediate Similarity	NPC476406
0.8286	Intermediate Similarity	NPC222366
0.8286	Intermediate Similarity	NPC476039
0.8267	Intermediate Similarity	NPC470749
0.8267	Intermediate Similarity	NPC167873
0.8267	Intermediate Similarity	NPC120098
0.8267	Intermediate Similarity	NPC30590
0.8267	Intermediate Similarity	NPC290598
0.8267	Intermediate Similarity	NPC107059
0.8267	Intermediate Similarity	NPC265328
0.8267	Intermediate Similarity	NPC122418
0.8267	Intermediate Similarity	NPC1973
0.8267	Intermediate Similarity	NPC315261
0.8267	Intermediate Similarity	NPC113733
0.8267	Intermediate Similarity	NPC321381
0.8267	Intermediate Similarity	NPC321016
0.8267	Intermediate Similarity	NPC237460
0.8267	Intermediate Similarity	NPC470362
0.8267	Intermediate Similarity	NPC27765
0.8267	Intermediate Similarity	NPC189883
0.8261	Intermediate Similarity	NPC144650
0.8261	Intermediate Similarity	NPC290367
0.8243	Intermediate Similarity	NPC469593
0.8243	Intermediate Similarity	NPC469533
0.8243	Intermediate Similarity	NPC469534
0.8228	Intermediate Similarity	NPC477818
0.8219	Intermediate Similarity	NPC471272
0.8205	Intermediate Similarity	NPC249423
0.8205	Intermediate Similarity	NPC142163
0.8194	Intermediate Similarity	NPC167272
0.8194	Intermediate Similarity	NPC269877
0.8194	Intermediate Similarity	NPC210323
0.8182	Intermediate Similarity	NPC100906
0.8182	Intermediate Similarity	NPC53744
0.8182	Intermediate Similarity	NPC291379
0.8182	Intermediate Similarity	NPC472463
0.8182	Intermediate Similarity	NPC1319
0.8182	Intermediate Similarity	NPC470429
0.8182	Intermediate Similarity	NPC30986
0.8182	Intermediate Similarity	NPC209430
0.8169	Intermediate Similarity	NPC185874
0.8169	Intermediate Similarity	NPC139207
0.8169	Intermediate Similarity	NPC45782
0.8158	Intermediate Similarity	NPC470428
0.8158	Intermediate Similarity	NPC198968
0.8158	Intermediate Similarity	NPC318495
0.8158	Intermediate Similarity	NPC214570
0.8158	Intermediate Similarity	NPC155986
0.8143	Intermediate Similarity	NPC172613
0.8143	Intermediate Similarity	NPC60837
0.8143	Intermediate Similarity	NPC64123
0.8143	Intermediate Similarity	NPC2728
0.8143	Intermediate Similarity	NPC282619
0.8143	Intermediate Similarity	NPC208198
0.8143	Intermediate Similarity	NPC11555
0.8133	Intermediate Similarity	NPC230301
0.8133	Intermediate Similarity	NPC22105
0.8133	Intermediate Similarity	NPC138374
0.8133	Intermediate Similarity	NPC285893
0.8133	Intermediate Similarity	NPC288035
0.8133	Intermediate Similarity	NPC136188
0.8133	Intermediate Similarity	NPC32832
0.8133	Intermediate Similarity	NPC304309
0.8133	Intermediate Similarity	NPC28657
0.8133	Intermediate Similarity	NPC162742
0.8133	Intermediate Similarity	NPC134847
0.8133	Intermediate Similarity	NPC34700
0.8125	Intermediate Similarity	NPC238485
0.8125	Intermediate Similarity	NPC231310
0.8108	Intermediate Similarity	NPC130665
0.8101	Intermediate Similarity	NPC202389
0.8101	Intermediate Similarity	NPC20853
0.8101	Intermediate Similarity	NPC296701
0.8101	Intermediate Similarity	NPC201852
0.8101	Intermediate Similarity	NPC218616
0.8077	Intermediate Similarity	NPC164840
0.8077	Intermediate Similarity	NPC236112
0.8077	Intermediate Similarity	NPC295131
0.8077	Intermediate Similarity	NPC241290
0.8077	Intermediate Similarity	NPC234193
0.8077	Intermediate Similarity	NPC13554
0.8077	Intermediate Similarity	NPC209944
0.8077	Intermediate Similarity	NPC281880
0.8056	Intermediate Similarity	NPC160209
0.8056	Intermediate Similarity	NPC94192
0.8056	Intermediate Similarity	NPC2648
0.8056	Intermediate Similarity	NPC96484
0.8052	Intermediate Similarity	NPC312328
0.8052	Intermediate Similarity	NPC87604
0.8052	Intermediate Similarity	NPC275910
0.8052	Intermediate Similarity	NPC476949
0.8052	Intermediate Similarity	NPC65897
0.8052	Intermediate Similarity	NPC474216
0.8052	Intermediate Similarity	NPC85346
0.8052	Intermediate Similarity	NPC473943

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 NPC68443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1354
0.2-0.3	4028
0.3-0.4	2483
0.4-0.5	727
0.5-0.6	218
0.6-0.7	139
0.7-0.8	36
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8493	Intermediate Similarity	NPD6926	Approved
0.8493	Intermediate Similarity	NPD6924	Approved
0.8472	Intermediate Similarity	NPD7151	Approved
0.8472	Intermediate Similarity	NPD7152	Approved
0.8472	Intermediate Similarity	NPD7150	Approved
0.8378	Intermediate Similarity	NPD8264	Approved
0.8333	Intermediate Similarity	NPD7143	Approved
0.8333	Intermediate Similarity	NPD7144	Approved
0.8312	Intermediate Similarity	NPD7525	Registered
0.8312	Intermediate Similarity	NPD7509	Discontinued
0.8267	Intermediate Similarity	NPD6933	Approved
0.8194	Intermediate Similarity	NPD6923	Approved
0.8194	Intermediate Similarity	NPD6922	Approved
0.8182	Intermediate Similarity	NPD7645	Phase 2
0.8133	Intermediate Similarity	NPD6942	Approved
0.8133	Intermediate Similarity	NPD7339	Approved
0.8026	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6929	Approved
0.7922	Intermediate Similarity	NPD6932	Approved
0.7848	Intermediate Similarity	NPD6930	Phase 2
0.7848	Intermediate Similarity	NPD6931	Approved
0.7821	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7145	Approved
0.7692	Intermediate Similarity	NPD6925	Approved
0.7692	Intermediate Similarity	NPD5776	Phase 2
0.7683	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7332	Phase 2
0.7625	Intermediate Similarity	NPD7514	Phase 3
0.7561	Intermediate Similarity	NPD6695	Phase 3
0.7531	Intermediate Similarity	NPD6902	Approved
0.75	Intermediate Similarity	NPD6683	Phase 2
0.747	Intermediate Similarity	NPD4786	Approved
0.7439	Intermediate Similarity	NPD3667	Approved
0.7381	Intermediate Similarity	NPD6893	Approved
0.7317	Intermediate Similarity	NPD6898	Phase 1
0.7308	Intermediate Similarity	NPD4785	Approved
0.7308	Intermediate Similarity	NPD4784	Approved
0.7294	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD4243	Approved
0.7241	Intermediate Similarity	NPD5328	Approved
0.7209	Intermediate Similarity	NPD7524	Approved
0.7209	Intermediate Similarity	NPD7750	Discontinued
0.7093	Intermediate Similarity	NPD5279	Phase 3
0.7079	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4202	Approved
0.6988	Remote Similarity	NPD4748	Discontinued
0.6988	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7087	Discontinued
0.6889	Remote Similarity	NPD6411	Approved
0.6867	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD6399	Phase 3
0.679	Remote Similarity	NPD4190	Phase 3
0.679	Remote Similarity	NPD5275	Approved
0.6782	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7136	Phase 2
0.6774	Remote Similarity	NPD5221	Approved
0.6774	Remote Similarity	NPD5222	Approved
0.6774	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4219	Approved
0.6757	Remote Similarity	NPD368	Approved
0.6739	Remote Similarity	NPD7748	Approved
0.6737	Remote Similarity	NPD5285	Approved
0.6737	Remote Similarity	NPD5286	Approved
0.6737	Remote Similarity	NPD4696	Approved
0.6703	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD4755	Approved
0.6702	Remote Similarity	NPD7902	Approved
0.6702	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD5290	Discontinued
0.6598	Remote Similarity	NPD5211	Phase 2
0.6598	Remote Similarity	NPD5225	Approved
0.6598	Remote Similarity	NPD5224	Approved
0.6598	Remote Similarity	NPD5226	Approved
0.6598	Remote Similarity	NPD4633	Approved
0.6596	Remote Similarity	NPD4697	Phase 3
0.6588	Remote Similarity	NPD4695	Discontinued
0.6562	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD7640	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6543	Remote Similarity	NPD4732	Discontinued
0.6531	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD5174	Approved
0.6484	Remote Similarity	NPD4753	Phase 2
0.6465	Remote Similarity	NPD5141	Approved
0.6458	Remote Similarity	NPD4225	Approved
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6437	Remote Similarity	NPD4223	Phase 3
0.6437	Remote Similarity	NPD4221	Approved
0.6436	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD5329	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.64	Remote Similarity	NPD5739	Approved
0.6389	Remote Similarity	NPD342	Phase 1
0.6383	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7900	Approved
0.6375	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD4788	Approved
0.6344	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD5284	Approved
0.6344	Remote Similarity	NPD5281	Approved
0.6344	Remote Similarity	NPD8034	Phase 2
0.6337	Remote Similarity	NPD5697	Approved
0.6333	Remote Similarity	NPD7521	Approved
0.6333	Remote Similarity	NPD4694	Approved
0.6333	Remote Similarity	NPD6684	Approved
0.6333	Remote Similarity	NPD5330	Approved
0.6333	Remote Similarity	NPD7334	Approved
0.6333	Remote Similarity	NPD4623	Approved
0.6333	Remote Similarity	NPD5280	Approved
0.6333	Remote Similarity	NPD7146	Approved
0.6333	Remote Similarity	NPD6409	Approved
0.6333	Remote Similarity	NPD4519	Discontinued
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD7290	Approved
0.6311	Remote Similarity	NPD6883	Approved
0.6304	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4787	Phase 1
0.6292	Remote Similarity	NPD4197	Approved
0.6275	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD6011	Approved
0.6275	Remote Similarity	NPD4729	Approved
0.6275	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6238	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD4767	Approved
0.6222	Remote Similarity	NPD1696	Phase 3
0.622	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6013	Approved
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6012	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.6214	Remote Similarity	NPD6014	Approved
0.6196	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6903	Approved
0.619	Remote Similarity	NPD6882	Approved
0.619	Remote Similarity	NPD8297	Approved
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6084	Phase 2
0.6176	Remote Similarity	NPD5701	Approved
0.6173	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3617	Approved
0.6154	Remote Similarity	NPD5169	Approved
0.6154	Remote Similarity	NPD4688	Approved
0.6154	Remote Similarity	NPD4693	Phase 3
0.6154	Remote Similarity	NPD5135	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD5248	Approved
0.6154	Remote Similarity	NPD4689	Approved
0.6154	Remote Similarity	NPD4690	Approved
0.6154	Remote Similarity	NPD5205	Approved
0.6154	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD5249	Phase 3
0.6154	Remote Similarity	NPD4138	Approved
0.6154	Remote Similarity	NPD5250	Approved
0.6154	Remote Similarity	NPD5251	Approved
0.6154	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6051	Approved
0.6117	Remote Similarity	NPD5168	Approved
0.6117	Remote Similarity	NPD5128	Approved
0.6095	Remote Similarity	NPD5216	Approved
0.6095	Remote Similarity	NPD5217	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5215	Approved
0.6095	Remote Similarity	NPD5127	Approved
0.6087	Remote Similarity	NPD3573	Approved
0.6071	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4058	Approved
0.6067	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4096	Approved
0.6061	Remote Similarity	NPD6648	Approved
0.6047	Remote Similarity	NPD6116	Phase 1
0.6023	Remote Similarity	NPD5368	Approved
0.6023	Remote Similarity	NPD4822	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