NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	275.498
LogP:	1.294
LogD:	0.895
LogS:	-2.299
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	4.3
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.116
MDCK Permeability:	1.850260559876915e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.16
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	80.88237762451172%
Volume Distribution (VD):	0.285
Pgp-substrate:	21.961435317993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.237
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	3.266
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.72
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.843
Maximum Recommended Daily Dose:	0.462
Skin Sensitization:	0.508
Carcinogencity:	0.702
Eye Corrosion:	0.032
Eye Irritation:	0.606
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC472013

Natural Product ID:	NPC472013
*Common Name:**	(1R,7R,10S)-1-Hydroxy-3-Oxoguaia-4,11(13)-Dien-12-Oic Acid
IUPAC Name:	2-[(5R,8S,8aR)-8a-hydroxy-3,8-dimethyl-2-oxo-1,4,5,6,7,8-hexahydroazulen-5-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	PITQNBJHXKODTD-IYYOCNSZSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-5-11(9(2)14(17)18)6-12-10(3)13(16)7-15(8,12)19/h8,11,19H,2,4-7H2,1,3H3,(H,17,18)/t8-,11+,15+/m0/s1
SMILES:	CC1CCC(CC2=C(C(=O)CC12O)C)C(=C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3325481
PubChem CID:	91668306
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	Species	Asteraceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	180.0	nM	PMID[455220]

☑ 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 NPC472013 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	193
0.1-0.2	1456
0.2-0.3	7299
0.3-0.4	15589
0.4-0.5	10137
0.5-0.6	5827
0.6-0.7	1944
0.7-0.8	236
0.8-0.85	7
0.85-0.9	2
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476624
0.9595	High Similarity	NPC476627
0.9315	High Similarity	NPC7382
0.9241	High Similarity	NPC476628
0.92	High Similarity	NPC472014
0.9041	High Similarity	NPC29328
0.8684	High Similarity	NPC89374
0.8571	High Similarity	NPC182848
0.8514	High Similarity	NPC67608
0.8493	Intermediate Similarity	NPC476626
0.8272	Intermediate Similarity	NPC171665
0.8256	Intermediate Similarity	NPC77337
0.8158	Intermediate Similarity	NPC18543
0.8148	Intermediate Similarity	NPC233352
0.8148	Intermediate Similarity	NPC138492
0.8148	Intermediate Similarity	NPC824
0.7978	Intermediate Similarity	NPC167219
0.7952	Intermediate Similarity	NPC20262
0.7952	Intermediate Similarity	NPC256750
0.7931	Intermediate Similarity	NPC170775
0.7901	Intermediate Similarity	NPC192006
0.7895	Intermediate Similarity	NPC476614
0.7895	Intermediate Similarity	NPC476629
0.7882	Intermediate Similarity	NPC125290
0.7857	Intermediate Similarity	NPC65350
0.7821	Intermediate Similarity	NPC288667
0.7821	Intermediate Similarity	NPC469737
0.7821	Intermediate Similarity	NPC106309
0.7805	Intermediate Similarity	NPC301769
0.7805	Intermediate Similarity	NPC32758
0.7791	Intermediate Similarity	NPC472869
0.7753	Intermediate Similarity	NPC261607
0.7753	Intermediate Similarity	NPC300312
0.7753	Intermediate Similarity	NPC111114
0.775	Intermediate Similarity	NPC77501
0.7711	Intermediate Similarity	NPC74445
0.7711	Intermediate Similarity	NPC476625
0.7711	Intermediate Similarity	NPC287817
0.7701	Intermediate Similarity	NPC237540
0.7692	Intermediate Similarity	NPC280256
0.7683	Intermediate Similarity	NPC169095
0.7674	Intermediate Similarity	NPC261380
0.7667	Intermediate Similarity	NPC135776
0.7654	Intermediate Similarity	NPC25908
0.7654	Intermediate Similarity	NPC115719
0.7654	Intermediate Similarity	NPC141346
0.7654	Intermediate Similarity	NPC142759
0.7654	Intermediate Similarity	NPC473437
0.7654	Intermediate Similarity	NPC124289
0.764	Intermediate Similarity	NPC472866
0.7619	Intermediate Similarity	NPC78677
0.7619	Intermediate Similarity	NPC47031
0.7619	Intermediate Similarity	NPC59994
0.7614	Intermediate Similarity	NPC472870
0.7614	Intermediate Similarity	NPC72397
0.7609	Intermediate Similarity	NPC9812
0.759	Intermediate Similarity	NPC471890
0.759	Intermediate Similarity	NPC84185
0.759	Intermediate Similarity	NPC66677
0.7586	Intermediate Similarity	NPC476043
0.7561	Intermediate Similarity	NPC97377
0.7558	Intermediate Similarity	NPC472865
0.7558	Intermediate Similarity	NPC19849
0.7558	Intermediate Similarity	NPC248758
0.7558	Intermediate Similarity	NPC472864
0.7531	Intermediate Similarity	NPC472327
0.7529	Intermediate Similarity	NPC7414
0.7529	Intermediate Similarity	NPC85772
0.7529	Intermediate Similarity	NPC133844
0.7528	Intermediate Similarity	NPC268298
0.7527	Intermediate Similarity	NPC477949
0.75	Intermediate Similarity	NPC201658
0.75	Intermediate Similarity	NPC300940
0.75	Intermediate Similarity	NPC69271
0.75	Intermediate Similarity	NPC45495
0.75	Intermediate Similarity	NPC74673
0.75	Intermediate Similarity	NPC275098
0.75	Intermediate Similarity	NPC164218
0.7474	Intermediate Similarity	NPC206079
0.747	Intermediate Similarity	NPC198240
0.7447	Intermediate Similarity	NPC64742
0.7447	Intermediate Similarity	NPC141191
0.7447	Intermediate Similarity	NPC244411
0.7444	Intermediate Similarity	NPC71533
0.7444	Intermediate Similarity	NPC106510
0.7444	Intermediate Similarity	NPC145666
0.7444	Intermediate Similarity	NPC129419
0.7442	Intermediate Similarity	NPC97913
0.7442	Intermediate Similarity	NPC49019
0.7439	Intermediate Similarity	NPC279537
0.7419	Intermediate Similarity	NPC185553
0.7416	Intermediate Similarity	NPC117122
0.7412	Intermediate Similarity	NPC470241
0.7412	Intermediate Similarity	NPC325031
0.7403	Intermediate Similarity	NPC308294
0.7403	Intermediate Similarity	NPC322035
0.7403	Intermediate Similarity	NPC100719
0.7403	Intermediate Similarity	NPC142423
0.7403	Intermediate Similarity	NPC166791
0.7391	Intermediate Similarity	NPC470013
0.7391	Intermediate Similarity	NPC323008
0.7391	Intermediate Similarity	NPC477131
0.7391	Intermediate Similarity	NPC470010
0.7391	Intermediate Similarity	NPC262133
0.7391	Intermediate Similarity	NPC65829
0.7391	Intermediate Similarity	NPC53685
0.7386	Intermediate Similarity	NPC261721
0.7381	Intermediate Similarity	NPC469617
0.7381	Intermediate Similarity	NPC164308
0.7381	Intermediate Similarity	NPC7232
0.7381	Intermediate Similarity	NPC113363
0.7381	Intermediate Similarity	NPC201225
0.7375	Intermediate Similarity	NPC319163
0.7375	Intermediate Similarity	NPC67076
0.7356	Intermediate Similarity	NPC472958
0.7356	Intermediate Similarity	NPC472957
0.7356	Intermediate Similarity	NPC164577
0.7356	Intermediate Similarity	NPC165287
0.7356	Intermediate Similarity	NPC156485
0.7349	Intermediate Similarity	NPC61952
0.7349	Intermediate Similarity	NPC103987
0.7349	Intermediate Similarity	NPC53581
0.734	Intermediate Similarity	NPC169205
0.734	Intermediate Similarity	NPC108475
0.734	Intermediate Similarity	NPC213947
0.734	Intermediate Similarity	NPC170143
0.7333	Intermediate Similarity	NPC262043
0.7333	Intermediate Similarity	NPC232747
0.7333	Intermediate Similarity	NPC32922
0.7333	Intermediate Similarity	NPC477215
0.7333	Intermediate Similarity	NPC476388
0.7333	Intermediate Similarity	NPC52198
0.7333	Intermediate Similarity	NPC117405
0.7333	Intermediate Similarity	NPC205548
0.7317	Intermediate Similarity	NPC251435
0.7317	Intermediate Similarity	NPC244166
0.7312	Intermediate Similarity	NPC90121
0.7312	Intermediate Similarity	NPC48803
0.7312	Intermediate Similarity	NPC193645
0.7312	Intermediate Similarity	NPC304886
0.7312	Intermediate Similarity	NPC474490
0.7312	Intermediate Similarity	NPC275960
0.7308	Intermediate Similarity	NPC278895
0.7303	Intermediate Similarity	NPC476409
0.7303	Intermediate Similarity	NPC72513
0.7303	Intermediate Similarity	NPC136948
0.7294	Intermediate Similarity	NPC115418
0.7294	Intermediate Similarity	NPC271104
0.7292	Intermediate Similarity	NPC62670
0.7292	Intermediate Similarity	NPC477950
0.7292	Intermediate Similarity	NPC116139
0.7284	Intermediate Similarity	NPC215745
0.7284	Intermediate Similarity	NPC12815
0.7284	Intermediate Similarity	NPC238948
0.7284	Intermediate Similarity	NPC35656
0.7283	Intermediate Similarity	NPC472871
0.7273	Intermediate Similarity	NPC245434
0.7273	Intermediate Similarity	NPC165162
0.7273	Intermediate Similarity	NPC21471
0.7273	Intermediate Similarity	NPC474853
0.7273	Intermediate Similarity	NPC33570
0.7273	Intermediate Similarity	NPC474304
0.7273	Intermediate Similarity	NPC179006
0.7273	Intermediate Similarity	NPC142649
0.7273	Intermediate Similarity	NPC474329
0.7262	Intermediate Similarity	NPC74410
0.7262	Intermediate Similarity	NPC222210
0.7262	Intermediate Similarity	NPC63445
0.7253	Intermediate Similarity	NPC51486
0.725	Intermediate Similarity	NPC67183
0.7245	Intermediate Similarity	NPC100487
0.7241	Intermediate Similarity	NPC215294
0.7241	Intermediate Similarity	NPC477373
0.7234	Intermediate Similarity	NPC184065
0.7234	Intermediate Similarity	NPC29152
0.7229	Intermediate Similarity	NPC215481
0.7229	Intermediate Similarity	NPC472305
0.7229	Intermediate Similarity	NPC473223
0.7222	Intermediate Similarity	NPC472677
0.7222	Intermediate Similarity	NPC58532
0.7222	Intermediate Similarity	NPC91248
0.7222	Intermediate Similarity	NPC48107
0.7216	Intermediate Similarity	NPC66110
0.7204	Intermediate Similarity	NPC90453
0.7204	Intermediate Similarity	NPC198853
0.7204	Intermediate Similarity	NPC469632
0.7195	Intermediate Similarity	NPC206875
0.7191	Intermediate Similarity	NPC67493
0.7191	Intermediate Similarity	NPC186975
0.7191	Intermediate Similarity	NPC107787
0.7191	Intermediate Similarity	NPC194417
0.7188	Intermediate Similarity	NPC280963
0.7179	Intermediate Similarity	NPC197089
0.7174	Intermediate Similarity	NPC473986
0.7174	Intermediate Similarity	NPC131209
0.7174	Intermediate Similarity	NPC204341
0.7174	Intermediate Similarity	NPC472705
0.7174	Intermediate Similarity	NPC474018
0.7174	Intermediate Similarity	NPC284185
0.7174	Intermediate Similarity	NPC133698

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 NPC472013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	2230
0.2-0.3	3965
0.3-0.4	1907
0.4-0.5	585
0.5-0.6	230
0.6-0.7	35
0.7-0.8	5
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
0.7882	Intermediate Similarity	NPD5363	Approved
0.7529	Intermediate Similarity	NPD4269	Approved
0.7529	Intermediate Similarity	NPD4270	Approved
0.7444	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4252	Approved
0.7241	Intermediate Similarity	NPD5362	Discontinued
0.7209	Intermediate Similarity	NPD5369	Approved
0.7191	Intermediate Similarity	NPD5786	Approved
0.7126	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4820	Approved
0.6897	Remote Similarity	NPD4821	Approved
0.6897	Remote Similarity	NPD4819	Approved
0.6897	Remote Similarity	NPD4822	Approved
0.6854	Remote Similarity	NPD7154	Phase 3
0.6835	Remote Similarity	NPD7341	Phase 2
0.6813	Remote Similarity	NPD4519	Discontinued
0.6813	Remote Similarity	NPD4623	Approved
0.6809	Remote Similarity	NPD5284	Approved
0.6809	Remote Similarity	NPD5281	Approved
0.675	Remote Similarity	NPD7331	Phase 2
0.6742	Remote Similarity	NPD4221	Approved
0.6742	Remote Similarity	NPD5209	Approved
0.6742	Remote Similarity	NPD4223	Phase 3
0.6705	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.663	Remote Similarity	NPD5690	Phase 2
0.6629	Remote Similarity	NPD4790	Discontinued
0.6598	Remote Similarity	NPD5695	Phase 3
0.6596	Remote Similarity	NPD1695	Approved
0.6593	Remote Similarity	NPD4197	Approved
0.6556	Remote Similarity	NPD6435	Approved
0.6556	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4756	Discovery
0.6522	Remote Similarity	NPD5329	Approved
0.6517	Remote Similarity	NPD4695	Discontinued
0.6517	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6084	Phase 2
0.6465	Remote Similarity	NPD6083	Phase 2
0.6458	Remote Similarity	NPD5693	Phase 1
0.6452	Remote Similarity	NPD4688	Approved
0.6452	Remote Similarity	NPD5205	Approved
0.6452	Remote Similarity	NPD4694	Approved
0.6452	Remote Similarity	NPD4138	Approved
0.6452	Remote Similarity	NPD4689	Approved
0.6452	Remote Similarity	NPD4690	Approved
0.6452	Remote Similarity	NPD4693	Phase 3
0.6452	Remote Similarity	NPD5280	Approved
0.6421	Remote Similarity	NPD6904	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.6421	Remote Similarity	NPD6080	Approved
0.6421	Remote Similarity	NPD6673	Approved
0.6413	Remote Similarity	NPD3133	Approved
0.6413	Remote Similarity	NPD3666	Approved
0.6413	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD5696	Approved
0.6392	Remote Similarity	NPD5779	Approved
0.6392	Remote Similarity	NPD5778	Approved
0.6354	Remote Similarity	NPD5692	Phase 3
0.6344	Remote Similarity	NPD1694	Approved
0.6327	Remote Similarity	NPD5282	Discontinued
0.6316	Remote Similarity	NPD4518	Approved
0.6316	Remote Similarity	NPD5208	Approved
0.6292	Remote Similarity	NPD3617	Approved
0.6289	Remote Similarity	NPD5694	Approved
0.6289	Remote Similarity	NPD6050	Approved
0.6277	Remote Similarity	NPD7146	Approved
0.6277	Remote Similarity	NPD6409	Approved
0.6277	Remote Similarity	NPD5330	Approved
0.6277	Remote Similarity	NPD7521	Approved
0.6277	Remote Similarity	NPD6684	Approved
0.6277	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD857	Phase 3
0.6263	Remote Similarity	NPD4629	Approved
0.6263	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5370	Suspended
0.6238	Remote Similarity	NPD4225	Approved
0.6222	Remote Similarity	NPD4195	Approved
0.6216	Remote Similarity	NPD7115	Discovery
0.6214	Remote Similarity	NPD5211	Phase 2
0.6186	Remote Similarity	NPD5207	Approved
0.6186	Remote Similarity	NPD4096	Approved
0.6176	Remote Similarity	NPD6404	Discontinued
0.6173	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1696	Phase 3
0.617	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5737	Approved
0.6146	Remote Similarity	NPD6903	Approved
0.6146	Remote Similarity	NPD6672	Approved
0.6132	Remote Similarity	NPD5697	Approved
0.6129	Remote Similarity	NPD4788	Approved
0.6122	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD7983	Approved
0.6105	Remote Similarity	NPD5279	Phase 3
0.6105	Remote Similarity	NPD3618	Phase 1
0.6105	Remote Similarity	NPD4249	Approved
0.6105	Remote Similarity	NPD6098	Approved
0.61	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5141	Approved
0.6087	Remote Similarity	NPD4139	Approved
0.6087	Remote Similarity	NPD4692	Approved
0.6082	Remote Similarity	NPD6101	Approved
0.6082	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6011	Approved
0.6075	Remote Similarity	NPD6899	Approved
0.6075	Remote Similarity	NPD6881	Approved
0.6061	Remote Similarity	NPD4202	Approved
0.6061	Remote Similarity	NPD6399	Phase 3
0.6053	Remote Similarity	NPD3172	Approved
0.6042	Remote Similarity	NPD4251	Approved
0.6042	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD6675	Approved
0.6022	Remote Similarity	NPD3667	Approved
0.602	Remote Similarity	NPD46	Approved
0.602	Remote Similarity	NPD6698	Approved
0.6019	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD5285	Approved
0.6019	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD4696	Approved
0.6019	Remote Similarity	NPD7639	Approved
0.6019	Remote Similarity	NPD6014	Approved
0.6019	Remote Similarity	NPD6013	Approved
0.6019	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5981	Remote Similarity	NPD5701	Approved
0.598	Remote Similarity	NPD4755	Approved
0.5974	Remote Similarity	NPD3195	Phase 2
0.5974	Remote Similarity	NPD4266	Approved
0.5974	Remote Similarity	NPD3196	Approved
0.5974	Remote Similarity	NPD3194	Approved
0.5963	Remote Similarity	NPD7102	Approved
0.5963	Remote Similarity	NPD7290	Approved
0.5963	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD5223	Approved
0.596	Remote Similarity	NPD7637	Suspended
0.596	Remote Similarity	NPD6411	Approved
0.596	Remote Similarity	NPD6079	Approved
0.5941	Remote Similarity	NPD5654	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5922	Remote Similarity	NPD7638	Approved
0.5918	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD6650	Approved
0.5909	Remote Similarity	NPD6617	Approved
0.5909	Remote Similarity	NPD6869	Approved
0.5909	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD8130	Phase 1
0.5909	Remote Similarity	NPD6649	Approved
0.5905	Remote Similarity	NPD5091	Approved
0.5905	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD5224	Approved
0.5905	Remote Similarity	NPD5225	Approved
0.5905	Remote Similarity	NPD5226	Approved
0.59	Remote Similarity	NPD5133	Approved
0.5895	Remote Similarity	NPD4786	Approved
0.5882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7614	Phase 1
0.5882	Remote Similarity	NPD7839	Suspended
0.5882	Remote Similarity	NPD5221	Approved
0.5882	Remote Similarity	NPD5222	Approved
0.5872	Remote Similarity	NPD6372	Approved
0.5872	Remote Similarity	NPD6373	Approved
0.5865	Remote Similarity	NPD4700	Approved
0.5862	Remote Similarity	NPD4691	Approved
0.5856	Remote Similarity	NPD6882	Approved
0.5856	Remote Similarity	NPD8297	Approved
0.5849	Remote Similarity	NPD6647	Phase 2
0.5849	Remote Similarity	NPD5174	Approved
0.5849	Remote Similarity	NPD5175	Approved
0.5842	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5959	Approved
0.5825	Remote Similarity	NPD5173	Approved
0.5825	Remote Similarity	NPD7902	Approved
0.5818	Remote Similarity	NPD4634	Approved
0.5804	Remote Similarity	NPD4632	Approved
0.5802	Remote Similarity	NPD3198	Approved
0.578	Remote Similarity	NPD6686	Approved
0.5776	Remote Similarity	NPD6319	Approved
0.5769	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD634	Phase 3
0.5747	Remote Similarity	NPD4137	Phase 3
0.5729	Remote Similarity	NPD3668	Phase 3

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