NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	2.584
LogD:	2.865
LogS:	-1.934
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	3.987
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:	-4.506
MDCK Permeability:	1.0126632332685404e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.244
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.81
Plasma Protein Binding (PPB):	45.96685791015625%
Volume Distribution (VD):	0.75
Pgp-substrate:	60.02699279785156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.496
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	11.326
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.234
Carcinogencity:	0.089
Eye Corrosion:	0.355
Eye Irritation:	0.448
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC144650

Natural Product ID:	NPC144650
*Common Name:**	Isodrimenediol
IUPAC Name:	(2S,4aS,5S,8aR)-5-(hydroxymethyl)-1,1,4a-trimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-ol
Synonyms:	isodrimenediol
Standard InCHIKey:	PFTWUCXOLILHIQ-PWNZVWSESA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10-5-6-12-14(2,3)13(17)7-8-15(12,4)11(10)9-16/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m0/s1
SMILES:	OC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465199
PubChem CID:	10537922
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9046	Aigialus parvus	Species	Aigialaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO14259	Euphorbia milii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13752	Acacia mollissima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14259	Euphorbia milii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13752	Acacia mollissima	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5283	Schefflera actinophylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17993	Antitrogus parvulus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14259	Euphorbia milii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9046	Aigialus parvus	Species	Aigialaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO640	Gloriosa modesta	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12172	Bauerella baueri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15162	Henricia sanguinolenta	Species	Echinasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6091	Gluta usitata	Species	Anacardiaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10.0	ug.mL-1	PMID[511941]
NPT3474	Organism	Sporidiobolus salmonicolor	Sporidiobolus salmonicolor	MIC	=	5.0	ug.mL-1	PMID[511941]

☑ 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 NPC144650 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	178
0.1-0.2	1923
0.2-0.3	8801
0.3-0.4	16371
0.4-0.5	6923
0.5-0.6	5303
0.6-0.7	2487
0.7-0.8	596
0.8-0.85	77
0.85-0.9	23
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9508	High Similarity	NPC60837
0.9508	High Similarity	NPC2728
0.9508	High Similarity	NPC172613
0.9508	High Similarity	NPC208198
0.9508	High Similarity	NPC11555
0.9508	High Similarity	NPC282619
0.9355	High Similarity	NPC473929
0.9344	High Similarity	NPC101128
0.9206	High Similarity	NPC185874
0.9206	High Similarity	NPC253303
0.9206	High Similarity	NPC269077
0.9206	High Similarity	NPC139207
0.9062	High Similarity	NPC276616
0.9062	High Similarity	NPC244790
0.9032	High Similarity	NPC68656
0.8889	High Similarity	NPC258595
0.8806	High Similarity	NPC95165
0.8788	High Similarity	NPC92801
0.8769	High Similarity	NPC245795
0.875	High Similarity	NPC475897
0.8676	High Similarity	NPC243342
0.8676	High Similarity	NPC477138
0.8657	High Similarity	NPC167706
0.8636	High Similarity	NPC9942
0.8551	High Similarity	NPC291503
0.8551	High Similarity	NPC477923
0.8551	High Similarity	NPC66566
0.8529	High Similarity	NPC211009
0.8525	High Similarity	NPC189290
0.8525	High Similarity	NPC474769
0.8507	High Similarity	NPC283316
0.8507	High Similarity	NPC45296
0.8438	Intermediate Similarity	NPC219940
0.8406	Intermediate Similarity	NPC91858
0.8406	Intermediate Similarity	NPC472503
0.8406	Intermediate Similarity	NPC308440
0.8382	Intermediate Similarity	NPC301226
0.8382	Intermediate Similarity	NPC111234
0.8382	Intermediate Similarity	NPC164022
0.8382	Intermediate Similarity	NPC242001
0.8382	Intermediate Similarity	NPC477792
0.8358	Intermediate Similarity	NPC210323
0.8333	Intermediate Similarity	NPC67508
0.8333	Intermediate Similarity	NPC84824
0.831	Intermediate Similarity	NPC471798
0.831	Intermediate Similarity	NPC477924
0.8308	Intermediate Similarity	NPC300442
0.8286	Intermediate Similarity	NPC185536
0.8286	Intermediate Similarity	NPC144075
0.8286	Intermediate Similarity	NPC212879
0.8286	Intermediate Similarity	NPC230704
0.8286	Intermediate Similarity	NPC231256
0.8286	Intermediate Similarity	NPC3403
0.8286	Intermediate Similarity	NPC104387
0.8286	Intermediate Similarity	NPC240235
0.8286	Intermediate Similarity	NPC70982
0.8286	Intermediate Similarity	NPC178383
0.8261	Intermediate Similarity	NPC471799
0.8261	Intermediate Similarity	NPC182717
0.8261	Intermediate Similarity	NPC68443
0.8235	Intermediate Similarity	NPC145498
0.8209	Intermediate Similarity	NPC2648
0.8209	Intermediate Similarity	NPC208999
0.8209	Intermediate Similarity	NPC266578
0.8197	Intermediate Similarity	NPC264779
0.8194	Intermediate Similarity	NPC99168
0.8194	Intermediate Similarity	NPC470396
0.8194	Intermediate Similarity	NPC474989
0.8194	Intermediate Similarity	NPC22955
0.8182	Intermediate Similarity	NPC476406
0.8169	Intermediate Similarity	NPC477925
0.8169	Intermediate Similarity	NPC278091
0.8169	Intermediate Similarity	NPC63958
0.8169	Intermediate Similarity	NPC274079
0.8169	Intermediate Similarity	NPC86305
0.8169	Intermediate Similarity	NPC265588
0.8169	Intermediate Similarity	NPC93662
0.8169	Intermediate Similarity	NPC78067
0.8169	Intermediate Similarity	NPC14112
0.8169	Intermediate Similarity	NPC91573
0.8154	Intermediate Similarity	NPC225415
0.8143	Intermediate Similarity	NPC476366
0.8143	Intermediate Similarity	NPC49168
0.8143	Intermediate Similarity	NPC471797
0.8143	Intermediate Similarity	NPC201048
0.8143	Intermediate Similarity	NPC254509
0.8143	Intermediate Similarity	NPC62657
0.8143	Intermediate Similarity	NPC306727
0.8143	Intermediate Similarity	NPC145552
0.8143	Intermediate Similarity	NPC5046
0.8143	Intermediate Similarity	NPC196358
0.8143	Intermediate Similarity	NPC25511
0.8143	Intermediate Similarity	NPC100334
0.8143	Intermediate Similarity	NPC192638
0.8116	Intermediate Similarity	NPC242992
0.8088	Intermediate Similarity	NPC234511
0.8082	Intermediate Similarity	NPC53744
0.8082	Intermediate Similarity	NPC470429
0.8082	Intermediate Similarity	NPC291379
0.8082	Intermediate Similarity	NPC472463
0.8056	Intermediate Similarity	NPC40394
0.8056	Intermediate Similarity	NPC212241
0.8056	Intermediate Similarity	NPC101475
0.8056	Intermediate Similarity	NPC474433
0.8056	Intermediate Similarity	NPC470428
0.8056	Intermediate Similarity	NPC331618
0.8056	Intermediate Similarity	NPC470758
0.8056	Intermediate Similarity	NPC257191
0.8056	Intermediate Similarity	NPC202540
0.8056	Intermediate Similarity	NPC307336
0.8056	Intermediate Similarity	NPC119355
0.8056	Intermediate Similarity	NPC472805
0.8056	Intermediate Similarity	NPC470711
0.8056	Intermediate Similarity	NPC248830
0.8056	Intermediate Similarity	NPC34177
0.8056	Intermediate Similarity	NPC90979
0.8056	Intermediate Similarity	NPC91594
0.8056	Intermediate Similarity	NPC138502
0.8056	Intermediate Similarity	NPC260301
0.8056	Intermediate Similarity	NPC157996
0.803	Intermediate Similarity	NPC64123
0.8028	Intermediate Similarity	NPC200243
0.8	Intermediate Similarity	NPC265485
0.8	Intermediate Similarity	NPC195489
0.8	Intermediate Similarity	NPC220939
0.7973	Intermediate Similarity	NPC47149
0.7973	Intermediate Similarity	NPC71535
0.7973	Intermediate Similarity	NPC78545
0.7973	Intermediate Similarity	NPC287749
0.7973	Intermediate Similarity	NPC96362
0.7945	Intermediate Similarity	NPC472342
0.7945	Intermediate Similarity	NPC275910
0.7945	Intermediate Similarity	NPC301707
0.7945	Intermediate Similarity	NPC158662
0.7945	Intermediate Similarity	NPC230295
0.7945	Intermediate Similarity	NPC472501
0.7945	Intermediate Similarity	NPC477819
0.7945	Intermediate Similarity	NPC244385
0.7945	Intermediate Similarity	NPC477817
0.7945	Intermediate Similarity	NPC102708
0.7945	Intermediate Similarity	NPC42853
0.7945	Intermediate Similarity	NPC196753
0.7945	Intermediate Similarity	NPC167037
0.7945	Intermediate Similarity	NPC98386
0.7945	Intermediate Similarity	NPC138621
0.7945	Intermediate Similarity	NPC300499
0.7945	Intermediate Similarity	NPC476314
0.7945	Intermediate Similarity	NPC472499
0.7945	Intermediate Similarity	NPC253807
0.7945	Intermediate Similarity	NPC6978
0.7945	Intermediate Similarity	NPC285761
0.7945	Intermediate Similarity	NPC472500
0.7945	Intermediate Similarity	NPC31828
0.7945	Intermediate Similarity	NPC476949
0.7941	Intermediate Similarity	NPC96484
0.7941	Intermediate Similarity	NPC471238
0.7917	Intermediate Similarity	NPC290598
0.7917	Intermediate Similarity	NPC73875
0.7917	Intermediate Similarity	NPC240604
0.7917	Intermediate Similarity	NPC38141
0.7917	Intermediate Similarity	NPC106364
0.7917	Intermediate Similarity	NPC96319
0.7917	Intermediate Similarity	NPC265328
0.7917	Intermediate Similarity	NPC321016
0.7917	Intermediate Similarity	NPC321381
0.7917	Intermediate Similarity	NPC122418
0.7917	Intermediate Similarity	NPC253190
0.7917	Intermediate Similarity	NPC189883
0.7917	Intermediate Similarity	NPC300324
0.7917	Intermediate Similarity	NPC237460
0.7917	Intermediate Similarity	NPC106432
0.7917	Intermediate Similarity	NPC107059
0.7917	Intermediate Similarity	NPC470766
0.7917	Intermediate Similarity	NPC470749
0.7917	Intermediate Similarity	NPC30590
0.7917	Intermediate Similarity	NPC120098
0.7917	Intermediate Similarity	NPC27765
0.7887	Intermediate Similarity	NPC469534
0.7887	Intermediate Similarity	NPC469593
0.7887	Intermediate Similarity	NPC476736
0.7887	Intermediate Similarity	NPC469533
0.7879	Intermediate Similarity	NPC290367
0.7867	Intermediate Similarity	NPC157655
0.7867	Intermediate Similarity	NPC159148
0.7867	Intermediate Similarity	NPC142163
0.7867	Intermediate Similarity	NPC474531
0.7867	Intermediate Similarity	NPC328264
0.7867	Intermediate Similarity	NPC476646
0.7857	Intermediate Similarity	NPC471271
0.7857	Intermediate Similarity	NPC23954
0.7857	Intermediate Similarity	NPC110799
0.7857	Intermediate Similarity	NPC471268
0.7857	Intermediate Similarity	NPC471272
0.7838	Intermediate Similarity	NPC472742
0.7838	Intermediate Similarity	NPC1319
0.7838	Intermediate Similarity	NPC273410
0.7838	Intermediate Similarity	NPC475727
0.7838	Intermediate Similarity	NPC80530
0.7838	Intermediate Similarity	NPC49599
0.7838	Intermediate Similarity	NPC24504

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 NPC144650 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	2473
0.2-0.3	4059
0.3-0.4	1775
0.4-0.5	379
0.5-0.6	205
0.6-0.7	81
0.7-0.8	23
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
0.7917	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7645	Phase 2
0.7778	Intermediate Similarity	NPD7339	Approved
0.7778	Intermediate Similarity	NPD6942	Approved
0.7733	Intermediate Similarity	NPD7525	Registered
0.7639	Intermediate Similarity	NPD6926	Approved
0.7639	Intermediate Similarity	NPD6924	Approved
0.7432	Intermediate Similarity	NPD6933	Approved
0.7361	Intermediate Similarity	NPD7150	Approved
0.7361	Intermediate Similarity	NPD7151	Approved
0.7361	Intermediate Similarity	NPD7152	Approved
0.7324	Intermediate Similarity	NPD6923	Approved
0.7324	Intermediate Similarity	NPD6922	Approved
0.7308	Intermediate Similarity	NPD3667	Approved
0.7297	Intermediate Similarity	NPD8264	Approved
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.725	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7143	Approved
0.7222	Intermediate Similarity	NPD7144	Approved
0.716	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6929	Approved
0.7125	Intermediate Similarity	NPD4786	Approved
0.7051	Intermediate Similarity	NPD4748	Discontinued
0.7051	Intermediate Similarity	NPD6930	Phase 2
0.7051	Intermediate Similarity	NPD6931	Approved
0.7	Intermediate Similarity	NPD385	Approved
0.7	Intermediate Similarity	NPD384	Approved
0.6905	Remote Similarity	NPD5328	Approved
0.6883	Remote Similarity	NPD6925	Approved
0.6883	Remote Similarity	NPD6932	Approved
0.6883	Remote Similarity	NPD5776	Phase 2
0.6867	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7145	Approved
0.679	Remote Similarity	NPD6695	Phase 3
0.6744	Remote Similarity	NPD7515	Phase 2
0.6744	Remote Similarity	NPD6079	Approved
0.6711	Remote Similarity	NPD4785	Approved
0.6711	Remote Similarity	NPD4784	Approved
0.6709	Remote Similarity	NPD6683	Phase 2
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
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6627	Remote Similarity	NPD6893	Approved
0.6625	Remote Similarity	NPD7332	Phase 2
0.6625	Remote Similarity	NPD7514	Phase 3
0.6622	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4788	Approved
0.6571	Remote Similarity	NPD368	Approved
0.6552	Remote Similarity	NPD8034	Phase 2
0.6552	Remote Similarity	NPD8035	Phase 2
0.6543	Remote Similarity	NPD6898	Phase 1
0.6543	Remote Similarity	NPD6902	Approved
0.6533	Remote Similarity	NPD4787	Phase 1
0.6506	Remote Similarity	NPD3668	Phase 3
0.6484	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD7750	Discontinued
0.6471	Remote Similarity	NPD7524	Approved
0.6447	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4697	Phase 3
0.6444	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5221	Approved
0.6444	Remote Similarity	NPD5222	Approved
0.642	Remote Similarity	NPD4695	Discontinued
0.641	Remote Similarity	NPD5275	Approved
0.641	Remote Similarity	NPD3703	Phase 2
0.641	Remote Similarity	NPD4190	Phase 3
0.6404	Remote Similarity	NPD7748	Approved
0.6374	Remote Similarity	NPD4755	Approved
0.6374	Remote Similarity	NPD5173	Approved
0.6353	Remote Similarity	NPD5279	Phase 3
0.6329	Remote Similarity	NPD6117	Approved
0.6304	Remote Similarity	NPD5290	Discontinued
0.6304	Remote Similarity	NPD7638	Approved
0.6301	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4195	Approved
0.6292	Remote Similarity	NPD6399	Phase 3
0.6282	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6116	Phase 1
0.6237	Remote Similarity	NPD4696	Approved
0.6237	Remote Similarity	NPD5285	Approved
0.6237	Remote Similarity	NPD5286	Approved
0.6237	Remote Similarity	NPD7640	Approved
0.6237	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD4700	Approved
0.6197	Remote Similarity	NPD1145	Discontinued
0.6196	Remote Similarity	NPD7902	Approved
0.6184	Remote Similarity	NPD3698	Phase 2
0.618	Remote Similarity	NPD7087	Discontinued
0.6176	Remote Similarity	NPD342	Phase 1
0.6173	Remote Similarity	NPD6118	Approved
0.6173	Remote Similarity	NPD6114	Approved
0.6173	Remote Similarity	NPD6697	Approved
0.6173	Remote Similarity	NPD6115	Approved
0.617	Remote Similarity	NPD5223	Approved
0.6164	Remote Similarity	NPD371	Approved
0.6136	Remote Similarity	NPD4753	Phase 2
0.6105	Remote Similarity	NPD5224	Approved
0.6105	Remote Similarity	NPD5211	Phase 2
0.6105	Remote Similarity	NPD5225	Approved
0.6105	Remote Similarity	NPD4633	Approved
0.6105	Remote Similarity	NPD5226	Approved
0.6104	Remote Similarity	NPD4245	Approved
0.6104	Remote Similarity	NPD4244	Approved
0.6071	Remote Similarity	NPD4223	Phase 3
0.6071	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD5174	Approved
0.6042	Remote Similarity	NPD4754	Approved
0.6042	Remote Similarity	NPD5175	Approved
0.6032	Remote Similarity	NPD386	Approved
0.6032	Remote Similarity	NPD388	Approved
0.6024	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4159	Approved
0.6	Remote Similarity	NPD6411	Approved
0.5979	Remote Similarity	NPD5141	Approved
0.5977	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3617	Approved
0.5976	Remote Similarity	NPD3671	Phase 1
0.593	Remote Similarity	NPD4197	Approved
0.5918	Remote Similarity	NPD4767	Approved
0.5918	Remote Similarity	NPD6402	Approved
0.5918	Remote Similarity	NPD4768	Approved
0.5918	Remote Similarity	NPD6675	Approved
0.5918	Remote Similarity	NPD5739	Approved
0.5918	Remote Similarity	NPD7128	Approved
0.5897	Remote Similarity	NPD4789	Approved
0.5889	Remote Similarity	NPD7136	Phase 2
0.587	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7900	Approved
0.5862	Remote Similarity	NPD5329	Approved
0.5862	Remote Similarity	NPD1696	Phase 3
0.5859	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD5701	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	NPD6928	Phase 2
0.5824	Remote Similarity	NPD7637	Suspended
0.5806	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD4629	Approved
0.58	Remote Similarity	NPD6899	Approved
0.58	Remote Similarity	NPD5128	Approved
0.58	Remote Similarity	NPD5168	Approved
0.58	Remote Similarity	NPD4729	Approved
0.58	Remote Similarity	NPD6881	Approved
0.58	Remote Similarity	NPD7320	Approved
0.58	Remote Similarity	NPD6011	Approved
0.58	Remote Similarity	NPD4730	Approved
0.5795	Remote Similarity	NPD6409	Approved
0.5795	Remote Similarity	NPD7146	Approved
0.5795	Remote Similarity	NPD7334	Approved
0.5795	Remote Similarity	NPD6684	Approved
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
0.5795	Remote Similarity	NPD4623	Approved
0.5795	Remote Similarity	NPD4689	Approved
0.5795	Remote Similarity	NPD4519	Discontinued
0.5778	Remote Similarity	NPD6101	Approved
0.5778	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD7632	Discontinued
0.575	Remote Similarity	NPD4732	Discontinued
0.5743	Remote Similarity	NPD6012	Approved
0.5743	Remote Similarity	NPD6013	Approved
0.5743	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD6372	Approved
0.5743	Remote Similarity	NPD6014	Approved
0.5732	Remote Similarity	NPD1346	Approved
0.573	Remote Similarity	NPD3573	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5698	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5251	Approved
0.5686	Remote Similarity	NPD7102	Approved
0.5686	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD5247	Approved
0.5686	Remote Similarity	NPD5169	Approved
0.5686	Remote Similarity	NPD5135	Approved
0.5686	Remote Similarity	NPD4634	Approved
0.5686	Remote Similarity	NPD6883	Approved
0.5686	Remote Similarity	NPD5250	Approved
0.5686	Remote Similarity	NPD5249	Phase 3
0.5686	Remote Similarity	NPD7290	Approved
0.5686	Remote Similarity	NPD5248	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

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