NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	1.355
LogD:	0.923
LogS:	-2.106
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	4.441
Fsp3:	0.8
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:	-5.103
MDCK Permeability:	1.2195825547678396e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.131
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.545
Plasma Protein Binding (PPB):	68.24946594238281%
Volume Distribution (VD):	0.328
Pgp-substrate:	34.99235534667969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.617
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	4.473
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.3
Maximum Recommended Daily Dose:	0.151
Skin Sensitization:	0.911
Carcinogencity:	0.838
Eye Corrosion:	0.461
Eye Irritation:	0.945
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: NPC476625

Natural Product ID:	NPC476625
*Common Name:**	2-[(3S,3aR,5R,8S,8aS)-3,3a-dihydroxy-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoic acid
IUPAC Name:	2-[(3S,3aR,5R,8S,8aS)-3,3a-dihydroxy-3,8-dimethyl-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	ZMGBZTXMIOVCQH-BLSOKALJSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-9-4-5-11(10(2)13(16)17)8-15(19)12(9)6-7-14(15,3)18/h9,11-12,18-19H,2,4-8H2,1,3H3,(H,16,17)/t9-,11+,12-,14-,15+/m0/s1
SMILES:	C[C@H]1CC[C@H](C[C@]2([C@H]1CC[C@]2(C)O)O)C(=C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118711725
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
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2600	nM	PMID[25127164]
NPT2	Others	Unspecified		Activity	=	78.8	%	PMID[25127164]

☑ 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 NPC476625 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	202
0.1-0.2	2005
0.2-0.3	8691
0.3-0.4	16611
0.4-0.5	8459
0.5-0.6	5483
0.6-0.7	1107
0.7-0.8	135
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8214	Intermediate Similarity	NPC476628
0.8052	Intermediate Similarity	NPC18543
0.7849	Intermediate Similarity	NPC471381
0.7849	Intermediate Similarity	NPC186861
0.7831	Intermediate Similarity	NPC30675
0.7826	Intermediate Similarity	NPC471150
0.7802	Intermediate Similarity	NPC472873
0.7792	Intermediate Similarity	NPC476629
0.7791	Intermediate Similarity	NPC204105
0.7791	Intermediate Similarity	NPC284534
0.7791	Intermediate Similarity	NPC300082
0.7727	Intermediate Similarity	NPC178875
0.7727	Intermediate Similarity	NPC79549
0.7722	Intermediate Similarity	NPC469737
0.7711	Intermediate Similarity	NPC472013
0.7711	Intermediate Similarity	NPC476624
0.7683	Intermediate Similarity	NPC472014
0.7647	Intermediate Similarity	NPC133844
0.764	Intermediate Similarity	NPC215556
0.7634	Intermediate Similarity	NPC181151
0.7619	Intermediate Similarity	NPC156658
0.7619	Intermediate Similarity	NPC258965
0.7614	Intermediate Similarity	NPC118601
0.7614	Intermediate Similarity	NPC190753
0.7609	Intermediate Similarity	NPC476053
0.7609	Intermediate Similarity	NPC163228
0.7582	Intermediate Similarity	NPC258216
0.7561	Intermediate Similarity	NPC473437
0.7561	Intermediate Similarity	NPC124289
0.7561	Intermediate Similarity	NPC25908
0.7561	Intermediate Similarity	NPC141346
0.7561	Intermediate Similarity	NPC115719
0.7561	Intermediate Similarity	NPC142759
0.7558	Intermediate Similarity	NPC245665
0.7558	Intermediate Similarity	NPC107253
0.7556	Intermediate Similarity	NPC216284
0.7556	Intermediate Similarity	NPC246173
0.7553	Intermediate Similarity	NPC45125
0.75	Intermediate Similarity	NPC29328
0.7473	Intermediate Similarity	NPC155215
0.7471	Intermediate Similarity	NPC474780
0.7471	Intermediate Similarity	NPC151176
0.7471	Intermediate Similarity	NPC3464
0.7471	Intermediate Similarity	NPC475963
0.7449	Intermediate Similarity	NPC54737
0.7447	Intermediate Similarity	NPC311904
0.7444	Intermediate Similarity	NPC232747
0.7416	Intermediate Similarity	NPC270270
0.7407	Intermediate Similarity	NPC300940
0.7391	Intermediate Similarity	NPC153590
0.7391	Intermediate Similarity	NPC200237
0.7386	Intermediate Similarity	NPC329749
0.7381	Intermediate Similarity	NPC476627
0.7356	Intermediate Similarity	NPC111409
0.7356	Intermediate Similarity	NPC128246
0.7333	Intermediate Similarity	NPC207114
0.7333	Intermediate Similarity	NPC217983
0.7326	Intermediate Similarity	NPC126248
0.7326	Intermediate Similarity	NPC171665
0.7312	Intermediate Similarity	NPC90453
0.7303	Intermediate Similarity	NPC187661
0.7303	Intermediate Similarity	NPC56593
0.7303	Intermediate Similarity	NPC309757
0.7303	Intermediate Similarity	NPC474949
0.7303	Intermediate Similarity	NPC476015
0.7303	Intermediate Similarity	NPC470242
0.7303	Intermediate Similarity	NPC475019
0.7303	Intermediate Similarity	NPC474762
0.7303	Intermediate Similarity	NPC236692
0.7294	Intermediate Similarity	NPC84185
0.7294	Intermediate Similarity	NPC66677
0.7294	Intermediate Similarity	NPC471890
0.7283	Intermediate Similarity	NPC184063
0.7273	Intermediate Similarity	NPC194859
0.7273	Intermediate Similarity	NPC224386
0.7263	Intermediate Similarity	NPC474313
0.7253	Intermediate Similarity	NPC155935
0.7228	Intermediate Similarity	NPC139838
0.7228	Intermediate Similarity	NPC59489
0.7216	Intermediate Similarity	NPC150923
0.7216	Intermediate Similarity	NPC287539
0.7216	Intermediate Similarity	NPC3488
0.7204	Intermediate Similarity	NPC473263
0.7204	Intermediate Similarity	NPC473273
0.7204	Intermediate Similarity	NPC473234
0.7204	Intermediate Similarity	NPC475788
0.7204	Intermediate Similarity	NPC308656
0.7204	Intermediate Similarity	NPC60386
0.72	Intermediate Similarity	NPC310228
0.72	Intermediate Similarity	NPC52431
0.7191	Intermediate Similarity	NPC149725
0.7191	Intermediate Similarity	NPC304509
0.7191	Intermediate Similarity	NPC47958
0.7191	Intermediate Similarity	NPC137033
0.7188	Intermediate Similarity	NPC244411
0.7176	Intermediate Similarity	NPC63445
0.7176	Intermediate Similarity	NPC222210
0.7174	Intermediate Similarity	NPC35809
0.7174	Intermediate Similarity	NPC54065
0.7174	Intermediate Similarity	NPC19087
0.7174	Intermediate Similarity	NPC297474
0.7174	Intermediate Similarity	NPC37607
0.7174	Intermediate Similarity	NPC301969
0.7159	Intermediate Similarity	NPC11620
0.7158	Intermediate Similarity	NPC91771
0.7158	Intermediate Similarity	NPC142529
0.7143	Intermediate Similarity	NPC91248
0.7143	Intermediate Similarity	NPC153805
0.7128	Intermediate Similarity	NPC470013
0.7128	Intermediate Similarity	NPC470010
0.7128	Intermediate Similarity	NPC198853
0.7128	Intermediate Similarity	NPC262133
0.7128	Intermediate Similarity	NPC323008
0.7111	Intermediate Similarity	NPC67493
0.7108	Intermediate Similarity	NPC7382
0.71	Intermediate Similarity	NPC44004
0.71	Intermediate Similarity	NPC223450
0.71	Intermediate Similarity	NPC127235
0.71	Intermediate Similarity	NPC243998
0.7097	Intermediate Similarity	NPC35959
0.7097	Intermediate Similarity	NPC57304
0.7097	Intermediate Similarity	NPC133888
0.7097	Intermediate Similarity	NPC171360
0.7097	Intermediate Similarity	NPC293001
0.7097	Intermediate Similarity	NPC63193
0.7097	Intermediate Similarity	NPC29821
0.7079	Intermediate Similarity	NPC472957
0.7079	Intermediate Similarity	NPC472958
0.7071	Intermediate Similarity	NPC124881
0.7071	Intermediate Similarity	NPC37240
0.7065	Intermediate Similarity	NPC38392
0.7065	Intermediate Similarity	NPC173926
0.7065	Intermediate Similarity	NPC474951
0.7065	Intermediate Similarity	NPC472872
0.7059	Intermediate Similarity	NPC83108
0.7059	Intermediate Similarity	NPC214030
0.7053	Intermediate Similarity	NPC170120
0.7053	Intermediate Similarity	NPC52044
0.7053	Intermediate Similarity	NPC67584
0.7053	Intermediate Similarity	NPC475900
0.7051	Intermediate Similarity	NPC470325
0.7051	Intermediate Similarity	NPC53642
0.7045	Intermediate Similarity	NPC246076
0.7041	Intermediate Similarity	NPC116139
0.7041	Intermediate Similarity	NPC62670
0.7037	Intermediate Similarity	NPC67608
0.7033	Intermediate Similarity	NPC186148
0.7033	Intermediate Similarity	NPC248602
0.7033	Intermediate Similarity	NPC201658
0.7024	Intermediate Similarity	NPC89374
0.7024	Intermediate Similarity	NPC201263
0.7021	Intermediate Similarity	NPC135776
0.7021	Intermediate Similarity	NPC472874
0.7011	Intermediate Similarity	NPC164218
0.7011	Intermediate Similarity	NPC474981
0.7011	Intermediate Similarity	NPC51507
0.701	Intermediate Similarity	NPC221615
0.7	Intermediate Similarity	NPC287015
0.7	Intermediate Similarity	NPC476626
0.7	Intermediate Similarity	NPC146850
0.6989	Remote Similarity	NPC474761
0.6989	Remote Similarity	NPC476004
0.6979	Remote Similarity	NPC476009
0.6979	Remote Similarity	NPC9812
0.6979	Remote Similarity	NPC213078
0.697	Remote Similarity	NPC66110
0.697	Remote Similarity	NPC35185
0.697	Remote Similarity	NPC80144
0.697	Remote Similarity	NPC4899
0.697	Remote Similarity	NPC474730
0.697	Remote Similarity	NPC177013
0.6966	Remote Similarity	NPC65350
0.6961	Remote Similarity	NPC68248
0.6961	Remote Similarity	NPC117604
0.6957	Remote Similarity	NPC58219
0.6957	Remote Similarity	NPC177629
0.6957	Remote Similarity	NPC50847
0.6957	Remote Similarity	NPC202672
0.6957	Remote Similarity	NPC474471
0.6957	Remote Similarity	NPC315911
0.6957	Remote Similarity	NPC53158
0.6957	Remote Similarity	NPC281516
0.6957	Remote Similarity	NPC227379
0.6947	Remote Similarity	NPC473331
0.6947	Remote Similarity	NPC127019
0.6939	Remote Similarity	NPC280963
0.6939	Remote Similarity	NPC70865
0.6931	Remote Similarity	NPC170432
0.6923	Remote Similarity	NPC475007
0.6915	Remote Similarity	NPC471747
0.6915	Remote Similarity	NPC131209
0.6915	Remote Similarity	NPC286341
0.6915	Remote Similarity	NPC191339
0.6915	Remote Similarity	NPC133698
0.6915	Remote Similarity	NPC475925
0.6915	Remote Similarity	NPC235051
0.6907	Remote Similarity	NPC161493
0.6907	Remote Similarity	NPC477949
0.6907	Remote Similarity	NPC213947
0.6907	Remote Similarity	NPC108475

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 NPC476625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	2940
0.2-0.3	3932
0.3-0.4	1391
0.4-0.5	369
0.5-0.6	240
0.6-0.7	27
0.7-0.8	0
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
0.6778	Remote Similarity	NPD5362	Discontinued
0.663	Remote Similarity	NPD5363	Approved
0.6629	Remote Similarity	NPD5368	Approved
0.6559	Remote Similarity	NPD5786	Approved
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1695	Approved
0.6509	Remote Similarity	NPD6371	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4269	Approved
0.6484	Remote Similarity	NPD6435	Approved
0.6444	Remote Similarity	NPD4821	Approved
0.6444	Remote Similarity	NPD4822	Approved
0.6444	Remote Similarity	NPD4819	Approved
0.6444	Remote Similarity	NPD4820	Approved
0.6413	Remote Similarity	NPD5331	Approved
0.6413	Remote Similarity	NPD5332	Approved
0.6413	Remote Similarity	NPD4788	Approved
0.6404	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5284	Approved
0.6392	Remote Similarity	NPD5281	Approved
0.6374	Remote Similarity	NPD4790	Discontinued
0.6374	Remote Similarity	NPD5369	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6304	Remote Similarity	NPD4223	Phase 3
0.6304	Remote Similarity	NPD4221	Approved
0.6289	Remote Similarity	NPD5785	Approved
0.6264	Remote Similarity	NPD4252	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6222	Remote Similarity	NPD4268	Approved
0.6222	Remote Similarity	NPD4271	Approved
0.6211	Remote Similarity	NPD5690	Phase 2
0.6204	Remote Similarity	NPD4634	Approved
0.62	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5695	Phase 3
0.617	Remote Similarity	NPD4197	Approved
0.6154	Remote Similarity	NPD5211	Phase 2
0.6145	Remote Similarity	NPD7341	Phase 2
0.614	Remote Similarity	NPD6319	Approved
0.6125	Remote Similarity	NPD3198	Approved
0.6105	Remote Similarity	NPD5329	Approved
0.6105	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD6084	Phase 2
0.6078	Remote Similarity	NPD6083	Phase 2
0.6075	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD7331	Phase 2
0.6064	Remote Similarity	NPD7154	Phase 3
0.6061	Remote Similarity	NPD7983	Approved
0.6061	Remote Similarity	NPD5693	Phase 1
0.6042	Remote Similarity	NPD4138	Approved
0.6042	Remote Similarity	NPD4249	Approved
0.6042	Remote Similarity	NPD5205	Approved
0.6042	Remote Similarity	NPD4694	Approved
0.6042	Remote Similarity	NPD4689	Approved
0.6042	Remote Similarity	NPD4693	Phase 3
0.6042	Remote Similarity	NPD5280	Approved
0.6042	Remote Similarity	NPD4688	Approved
0.6042	Remote Similarity	NPD4690	Approved
0.6038	Remote Similarity	NPD5141	Approved
0.602	Remote Similarity	NPD4753	Phase 2
0.602	Remote Similarity	NPD6904	Approved
0.602	Remote Similarity	NPD6080	Approved
0.602	Remote Similarity	NPD6673	Approved
0.6019	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD6881	Approved
0.6019	Remote Similarity	NPD6899	Approved
0.6018	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5981	Remote Similarity	NPD6675	Approved
0.5981	Remote Similarity	NPD5739	Approved
0.5981	Remote Similarity	NPD7128	Approved
0.5981	Remote Similarity	NPD6402	Approved
0.5979	Remote Similarity	NPD4251	Approved
0.5979	Remote Similarity	NPD4250	Approved
0.5963	Remote Similarity	NPD6013	Approved
0.5963	Remote Similarity	NPD6014	Approved
0.5963	Remote Similarity	NPD6012	Approved
0.5962	Remote Similarity	NPD4696	Approved
0.5962	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD5692	Phase 3
0.5946	Remote Similarity	NPD8297	Approved
0.5938	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5701	Approved
0.5922	Remote Similarity	NPD4755	Approved
0.5918	Remote Similarity	NPD4518	Approved
0.5918	Remote Similarity	NPD5208	Approved
0.5909	Remote Similarity	NPD6883	Approved
0.5909	Remote Similarity	NPD7102	Approved
0.5909	Remote Similarity	NPD7290	Approved
0.5905	Remote Similarity	NPD5223	Approved
0.59	Remote Similarity	NPD5694	Approved
0.59	Remote Similarity	NPD6050	Approved
0.5889	Remote Similarity	NPD3702	Approved
0.5882	Remote Similarity	NPD4629	Approved
0.5882	Remote Similarity	NPD5210	Approved
0.5876	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6098	Approved
0.5872	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD6869	Approved
0.5856	Remote Similarity	NPD8130	Phase 1
0.5856	Remote Similarity	NPD6650	Approved
0.5856	Remote Similarity	NPD6617	Approved
0.5856	Remote Similarity	NPD6649	Approved
0.5856	Remote Similarity	NPD6847	Approved
0.5851	Remote Similarity	NPD4692	Approved
0.5851	Remote Similarity	NPD4139	Approved
0.5849	Remote Similarity	NPD5225	Approved
0.5849	Remote Similarity	NPD5226	Approved
0.5849	Remote Similarity	NPD5224	Approved
0.5849	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD3666	Approved
0.5833	Remote Similarity	NPD3665	Phase 1
0.5833	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD7909	Approved
0.5833	Remote Similarity	NPD3133	Approved
0.5818	Remote Similarity	NPD6373	Approved
0.5818	Remote Similarity	NPD6372	Approved
0.5812	Remote Similarity	NPD5983	Phase 2
0.581	Remote Similarity	NPD7640	Approved
0.581	Remote Similarity	NPD7639	Approved
0.581	Remote Similarity	NPD4700	Approved
0.5806	Remote Similarity	NPD4195	Approved
0.5804	Remote Similarity	NPD6882	Approved
0.58	Remote Similarity	NPD6698	Approved
0.58	Remote Similarity	NPD5207	Approved
0.58	Remote Similarity	NPD4096	Approved
0.58	Remote Similarity	NPD46	Approved
0.5798	Remote Similarity	NPD7492	Approved
0.5794	Remote Similarity	NPD5175	Approved
0.5794	Remote Similarity	NPD5174	Approved
0.575	Remote Similarity	NPD6616	Approved
0.575	Remote Similarity	NPD7507	Approved
0.5743	Remote Similarity	NPD8035	Phase 2
0.5743	Remote Similarity	NPD6079	Approved
0.5743	Remote Similarity	NPD8034	Phase 2
0.5728	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD7334	Approved
0.5702	Remote Similarity	NPD7078	Approved
0.57	Remote Similarity	NPD5328	Approved
0.5699	Remote Similarity	NPD4802	Phase 2
0.5699	Remote Similarity	NPD4238	Approved
0.5686	Remote Similarity	NPD4202	Approved
0.5686	Remote Similarity	NPD6399	Phase 3
0.5684	Remote Similarity	NPD857	Phase 3
0.5678	Remote Similarity	NPD6016	Approved
0.5678	Remote Similarity	NPD6015	Approved
0.5676	Remote Similarity	NPD634	Phase 3
0.5673	Remote Similarity	NPD5221	Approved
0.5673	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD6404	Discontinued
0.5656	Remote Similarity	NPD7736	Approved
0.5652	Remote Similarity	NPD6274	Approved
0.5648	Remote Similarity	NPD4754	Approved
0.5636	Remote Similarity	NPD6412	Phase 2
0.5631	Remote Similarity	NPD6001	Approved
0.563	Remote Similarity	NPD5988	Approved
0.563	Remote Similarity	NPD6370	Approved
0.5625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6336	Discontinued
0.5619	Remote Similarity	NPD5173	Approved
0.5614	Remote Similarity	NPD8133	Approved
0.561	Remote Similarity	NPD7319	Approved
0.5603	Remote Similarity	NPD6317	Approved
0.5603	Remote Similarity	NPD7115	Discovery
0.56	Remote Similarity	NPD5737	Approved
0.56	Remote Similarity	NPD6672	Approved
0.56	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.56	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