NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	202.05
Volume:	216.396
LogP:	3.144
LogD:	2.264
LogS:	-3.655
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.692
Synthetic Accessibility Score:	3.634
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-3.759
MDCK Permeability:	1.854780020948965e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.078
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	100.8636245727539%
Volume Distribution (VD):	1.468
Pgp-substrate:	1.4957592487335205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.762
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.528
CYP2C9-inhibitor:	0.935
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	6.892
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.612
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.943
Carcinogencity:	0.834
Eye Corrosion:	0.874
Eye Irritation:	0.992
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC275098

Natural Product ID:	NPC275098
*Common Name:**	(3R,6R,7S)-3,6-Dihydroxygermacra-4(5)E,10(14)-Dien-1-One
IUPAC Name:	(3R,4E,6R,7S)-3,6-dihydroxy-4-methyl-10-methylidene-7-propan-2-ylcyclodec-4-en-1-one
Synonyms:
Standard InCHIKey:	YAWLERPORBAXAE-TUUMZQRUSA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-9(2)12-6-5-10(3)13(16)8-14(17)11(4)7-15(12)18/h7,9,12,14-15,17-18H,3,5-6,8H2,1-2,4H3/b11-7+/t12-,14+,15-/m0/s1
SMILES:	CC([C@@H]1CCC(=C)C(=O)C[C@H](/C(=C/[C@@H]1O)/C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457809
PubChem CID:	11368769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002456] Germacrane sesquiterpenoids

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29822	Santolina insularis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15974607]
NPO29822	Santolina insularis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15974607]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		IC50	>=	10.0	ug.mL-1	PMID[505273]

☑ 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 NPC275098 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	179
0.1-0.2	1263
0.2-0.3	6494
0.3-0.4	15840
0.4-0.5	10249
0.5-0.6	6078
0.6-0.7	2198
0.7-0.8	366
0.8-0.85	28
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8289	Intermediate Similarity	NPC475994
0.8286	Intermediate Similarity	NPC197089
0.825	Intermediate Similarity	NPC261380
0.8182	Intermediate Similarity	NPC7232
0.8143	Intermediate Similarity	NPC474329
0.8143	Intermediate Similarity	NPC474304
0.8101	Intermediate Similarity	NPC85772
0.8077	Intermediate Similarity	NPC148685
0.8077	Intermediate Similarity	NPC45495
0.8077	Intermediate Similarity	NPC104120
0.8077	Intermediate Similarity	NPC157895
0.8052	Intermediate Similarity	NPC192006
0.8052	Intermediate Similarity	NPC478122
0.8026	Intermediate Similarity	NPC469646
0.7949	Intermediate Similarity	NPC308038
0.7949	Intermediate Similarity	NPC89128
0.7945	Intermediate Similarity	NPC10758
0.7945	Intermediate Similarity	NPC250928
0.7927	Intermediate Similarity	NPC194417
0.7922	Intermediate Similarity	NPC471061
0.7922	Intermediate Similarity	NPC86917
0.7922	Intermediate Similarity	NPC74995
0.7901	Intermediate Similarity	NPC141193
0.7901	Intermediate Similarity	NPC96259
0.7895	Intermediate Similarity	NPC474011
0.7867	Intermediate Similarity	NPC186042
0.7857	Intermediate Similarity	NPC473508
0.7848	Intermediate Similarity	NPC470946
0.7848	Intermediate Similarity	NPC470947
0.7848	Intermediate Similarity	NPC271104
0.7848	Intermediate Similarity	NPC470945
0.7826	Intermediate Similarity	NPC99487
0.7821	Intermediate Similarity	NPC196653
0.7821	Intermediate Similarity	NPC471465
0.7821	Intermediate Similarity	NPC62336
0.7805	Intermediate Similarity	NPC474853
0.7805	Intermediate Similarity	NPC179006
0.7794	Intermediate Similarity	NPC155025
0.7792	Intermediate Similarity	NPC263582
0.7792	Intermediate Similarity	NPC279537
0.7763	Intermediate Similarity	NPC7382
0.775	Intermediate Similarity	NPC47031
0.7746	Intermediate Similarity	NPC300593
0.7738	Intermediate Similarity	NPC476803
0.7738	Intermediate Similarity	NPC476805
0.7722	Intermediate Similarity	NPC19900
0.7722	Intermediate Similarity	NPC152061
0.7711	Intermediate Similarity	NPC476043
0.7692	Intermediate Similarity	NPC276769
0.7692	Intermediate Similarity	NPC211279
0.7683	Intermediate Similarity	NPC114979
0.7683	Intermediate Similarity	NPC7927
0.7683	Intermediate Similarity	NPC230527
0.7683	Intermediate Similarity	NPC191476
0.7683	Intermediate Similarity	NPC158756
0.7683	Intermediate Similarity	NPC476804
0.7671	Intermediate Similarity	NPC278895
0.7662	Intermediate Similarity	NPC114236
0.7662	Intermediate Similarity	NPC474885
0.7654	Intermediate Similarity	NPC93590
0.7654	Intermediate Similarity	NPC38796
0.7654	Intermediate Similarity	NPC7414
0.7654	Intermediate Similarity	NPC158411
0.7647	Intermediate Similarity	NPC170775
0.7625	Intermediate Similarity	NPC172013
0.7595	Intermediate Similarity	NPC297996
0.7595	Intermediate Similarity	NPC231739
0.759	Intermediate Similarity	NPC470755
0.759	Intermediate Similarity	NPC15807
0.759	Intermediate Similarity	NPC255307
0.759	Intermediate Similarity	NPC28887
0.759	Intermediate Similarity	NPC476426
0.759	Intermediate Similarity	NPC125290
0.7564	Intermediate Similarity	NPC271070
0.7564	Intermediate Similarity	NPC470525
0.7561	Intermediate Similarity	NPC477785
0.7561	Intermediate Similarity	NPC477784
0.7561	Intermediate Similarity	NPC477786
0.7558	Intermediate Similarity	NPC145666
0.7534	Intermediate Similarity	NPC311736
0.7532	Intermediate Similarity	NPC215050
0.7531	Intermediate Similarity	NPC24417
0.7531	Intermediate Similarity	NPC52861
0.7531	Intermediate Similarity	NPC116797
0.7531	Intermediate Similarity	NPC470241
0.7529	Intermediate Similarity	NPC474854
0.7528	Intermediate Similarity	NPC184065
0.75	Intermediate Similarity	NPC98557
0.75	Intermediate Similarity	NPC201225
0.75	Intermediate Similarity	NPC469910
0.75	Intermediate Similarity	NPC67076
0.75	Intermediate Similarity	NPC198761
0.75	Intermediate Similarity	NPC319163
0.75	Intermediate Similarity	NPC288667
0.75	Intermediate Similarity	NPC475461
0.75	Intermediate Similarity	NPC261721
0.75	Intermediate Similarity	NPC470955
0.75	Intermediate Similarity	NPC29328
0.75	Intermediate Similarity	NPC305475
0.75	Intermediate Similarity	NPC474884
0.75	Intermediate Similarity	NPC167881
0.75	Intermediate Similarity	NPC281138
0.75	Intermediate Similarity	NPC476624
0.75	Intermediate Similarity	NPC472974
0.75	Intermediate Similarity	NPC472013
0.7471	Intermediate Similarity	NPC476705
0.747	Intermediate Similarity	NPC472326
0.747	Intermediate Similarity	NPC476412
0.7468	Intermediate Similarity	NPC7563
0.7468	Intermediate Similarity	NPC320630
0.7468	Intermediate Similarity	NPC197659
0.7468	Intermediate Similarity	NPC116177
0.7468	Intermediate Similarity	NPC476007
0.7468	Intermediate Similarity	NPC473536
0.7468	Intermediate Similarity	NPC203403
0.7467	Intermediate Similarity	NPC477449
0.7467	Intermediate Similarity	NPC477448
0.7467	Intermediate Similarity	NPC67608
0.7465	Intermediate Similarity	NPC64985
0.7465	Intermediate Similarity	NPC225342
0.7439	Intermediate Similarity	NPC145963
0.7439	Intermediate Similarity	NPC133844
0.7439	Intermediate Similarity	NPC229825
0.7439	Intermediate Similarity	NPC279186
0.7436	Intermediate Similarity	NPC155587
0.7436	Intermediate Similarity	NPC199445
0.7436	Intermediate Similarity	NPC472256
0.7436	Intermediate Similarity	NPC89374
0.7436	Intermediate Similarity	NPC60718
0.7432	Intermediate Similarity	NPC472875
0.7432	Intermediate Similarity	NPC163290
0.7429	Intermediate Similarity	NPC122239
0.7407	Intermediate Similarity	NPC824
0.7407	Intermediate Similarity	NPC471514
0.7407	Intermediate Similarity	NPC115418
0.7407	Intermediate Similarity	NPC233352
0.7407	Intermediate Similarity	NPC306095
0.7407	Intermediate Similarity	NPC472301
0.7407	Intermediate Similarity	NPC138492
0.7397	Intermediate Similarity	NPC308844
0.7386	Intermediate Similarity	NPC475302
0.7381	Intermediate Similarity	NPC165162
0.7381	Intermediate Similarity	NPC70685
0.7381	Intermediate Similarity	NPC187529
0.7375	Intermediate Similarity	NPC321180
0.7375	Intermediate Similarity	NPC121200
0.7375	Intermediate Similarity	NPC476627
0.7375	Intermediate Similarity	NPC178852
0.7368	Intermediate Similarity	NPC286154
0.7356	Intermediate Similarity	NPC469368
0.7356	Intermediate Similarity	NPC230332
0.7349	Intermediate Similarity	NPC473390
0.7349	Intermediate Similarity	NPC40746
0.7349	Intermediate Similarity	NPC297398
0.7349	Intermediate Similarity	NPC169575
0.7349	Intermediate Similarity	NPC69469
0.7349	Intermediate Similarity	NPC131669
0.7349	Intermediate Similarity	NPC105173
0.7349	Intermediate Similarity	NPC62214
0.7342	Intermediate Similarity	NPC472305
0.7342	Intermediate Similarity	NPC61863
0.7342	Intermediate Similarity	NPC235906
0.7342	Intermediate Similarity	NPC7629
0.7342	Intermediate Similarity	NPC151622
0.7333	Intermediate Similarity	NPC117804
0.7333	Intermediate Similarity	NPC476614
0.7333	Intermediate Similarity	NPC469688
0.7326	Intermediate Similarity	NPC475819
0.7317	Intermediate Similarity	NPC6663
0.7317	Intermediate Similarity	NPC171665
0.7317	Intermediate Similarity	NPC14151
0.7317	Intermediate Similarity	NPC325031
0.7308	Intermediate Similarity	NPC227814
0.7308	Intermediate Similarity	NPC206875
0.7308	Intermediate Similarity	NPC472966
0.7308	Intermediate Similarity	NPC476649
0.7308	Intermediate Similarity	NPC144995
0.7303	Intermediate Similarity	NPC65829
0.7297	Intermediate Similarity	NPC308294
0.7297	Intermediate Similarity	NPC142423
0.7294	Intermediate Similarity	NPC472986
0.7294	Intermediate Similarity	NPC472985
0.7294	Intermediate Similarity	NPC316426
0.7294	Intermediate Similarity	NPC315395
0.7284	Intermediate Similarity	NPC470244
0.7284	Intermediate Similarity	NPC164308
0.7284	Intermediate Similarity	NPC261125
0.7284	Intermediate Similarity	NPC181195
0.7284	Intermediate Similarity	NPC113363
0.7284	Intermediate Similarity	NPC470239
0.7283	Intermediate Similarity	NPC306856
0.7273	Intermediate Similarity	NPC129665
0.7273	Intermediate Similarity	NPC472254
0.7273	Intermediate Similarity	NPC111114
0.7273	Intermediate Similarity	NPC300312
0.7273	Intermediate Similarity	NPC172101
0.7273	Intermediate Similarity	NPC472814
0.7273	Intermediate Similarity	NPC177037
0.7273	Intermediate Similarity	NPC261607
0.7262	Intermediate Similarity	NPC472958

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 NPC275098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1990
0.2-0.3	3944
0.3-0.4	2129
0.4-0.5	600
0.5-0.6	251
0.6-0.7	52
0.7-0.8	10
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
0.7805	Intermediate Similarity	NPD5363	Approved
0.7654	Intermediate Similarity	NPD4270	Approved
0.7654	Intermediate Similarity	NPD4269	Approved
0.7407	Intermediate Similarity	NPD4252	Approved
0.7375	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5785	Approved
0.7294	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7108	Intermediate Similarity	NPD5369	Approved
0.7067	Intermediate Similarity	NPD7331	Phase 2
0.6986	Remote Similarity	NPD368	Approved
0.6941	Remote Similarity	NPD7154	Phase 3
0.686	Remote Similarity	NPD3665	Phase 1
0.686	Remote Similarity	NPD3133	Approved
0.686	Remote Similarity	NPD3666	Approved
0.6848	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3667	Approved
0.6813	Remote Similarity	NPD5779	Approved
0.6813	Remote Similarity	NPD5778	Approved
0.6786	Remote Similarity	NPD4820	Approved
0.6786	Remote Similarity	NPD4821	Approved
0.6786	Remote Similarity	NPD5368	Approved
0.6786	Remote Similarity	NPD4822	Approved
0.6786	Remote Similarity	NPD4819	Approved
0.6747	Remote Similarity	NPD4268	Approved
0.6747	Remote Similarity	NPD4271	Approved
0.6744	Remote Similarity	NPD5332	Approved
0.6744	Remote Similarity	NPD5331	Approved
0.6711	Remote Similarity	NPD7341	Phase 2
0.6706	Remote Similarity	NPD4790	Discontinued
0.6705	Remote Similarity	NPD5279	Phase 3
0.6705	Remote Similarity	NPD3618	Phase 1
0.6703	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6628	Remote Similarity	NPD6435	Approved
0.662	Remote Similarity	NPD342	Phase 1
0.6591	Remote Similarity	NPD1696	Phase 3
0.6588	Remote Similarity	NPD4695	Discontinued
0.6588	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6079	Approved
0.6517	Remote Similarity	NPD4623	Approved
0.6517	Remote Similarity	NPD4519	Discontinued
0.6484	Remote Similarity	NPD6101	Approved
0.6484	Remote Similarity	NPD5328	Approved
0.6484	Remote Similarity	NPD5370	Suspended
0.6484	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5209	Approved
0.6437	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4756	Discovery
0.6421	Remote Similarity	NPD7839	Suspended
0.6413	Remote Similarity	NPD6698	Approved
0.6413	Remote Similarity	NPD46	Approved
0.6404	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD6110	Phase 1
0.6364	Remote Similarity	NPD3197	Phase 1
0.6344	Remote Similarity	NPD6411	Approved
0.6344	Remote Similarity	NPD7515	Phase 2
0.6344	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6371	Approved
0.6304	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD4225	Approved
0.6277	Remote Similarity	NPD4202	Approved
0.6263	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD4221	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5221	Approved
0.6222	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3704	Approved
0.619	Remote Similarity	NPD8264	Approved
0.6186	Remote Similarity	NPD5173	Approved
0.618	Remote Similarity	NPD4788	Approved
0.617	Remote Similarity	NPD7637	Suspended
0.6163	Remote Similarity	NPD3732	Approved
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD4249	Approved
0.6146	Remote Similarity	NPD4629	Approved
0.6146	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD4197	Approved
0.6111	Remote Similarity	NPD3172	Approved
0.6087	Remote Similarity	NPD4250	Approved
0.6087	Remote Similarity	NPD4251	Approved
0.6082	Remote Similarity	NPD4697	Phase 3
0.6076	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5285	Approved
0.6061	Remote Similarity	NPD4696	Approved
0.6061	Remote Similarity	NPD5286	Approved
0.6044	Remote Similarity	NPD5329	Approved
0.6042	Remote Similarity	NPD7748	Approved
0.6027	Remote Similarity	NPD4266	Approved
0.6027	Remote Similarity	NPD3194	Approved
0.6027	Remote Similarity	NPD3196	Approved
0.6027	Remote Similarity	NPD3195	Phase 2
0.602	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8039	Approved
0.5978	Remote Similarity	NPD4694	Approved
0.5978	Remote Similarity	NPD4688	Approved
0.5978	Remote Similarity	NPD5330	Approved
0.5978	Remote Similarity	NPD6684	Approved
0.5978	Remote Similarity	NPD7334	Approved
0.5978	Remote Similarity	NPD5280	Approved
0.5978	Remote Similarity	NPD7146	Approved
0.5978	Remote Similarity	NPD4693	Phase 3
0.5978	Remote Similarity	NPD4689	Approved
0.5978	Remote Similarity	NPD7521	Approved
0.5978	Remote Similarity	NPD4690	Approved
0.5978	Remote Similarity	NPD4138	Approved
0.5978	Remote Similarity	NPD5205	Approved
0.5978	Remote Similarity	NPD6409	Approved
0.5977	Remote Similarity	NPD3617	Approved
0.5977	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7115	Discovery
0.5957	Remote Similarity	NPD1695	Approved
0.5946	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4633	Approved
0.5941	Remote Similarity	NPD5224	Approved
0.5941	Remote Similarity	NPD5225	Approved
0.5941	Remote Similarity	NPD5226	Approved
0.5938	Remote Similarity	NPD6399	Phase 3
0.5926	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6929	Approved
0.5904	Remote Similarity	NPD4691	Approved
0.59	Remote Similarity	NPD4700	Approved
0.59	Remote Similarity	NPD7639	Approved
0.59	Remote Similarity	NPD7640	Approved
0.5895	Remote Similarity	NPD7838	Discovery
0.5882	Remote Similarity	NPD5175	Approved
0.5882	Remote Similarity	NPD5174	Approved
0.5882	Remote Similarity	NPD6926	Approved
0.5882	Remote Similarity	NPD6924	Approved
0.5882	Remote Similarity	NPD6647	Phase 2
0.5862	Remote Similarity	NPD5776	Phase 2
0.5862	Remote Similarity	NPD6925	Approved
0.5859	Remote Similarity	NPD6084	Phase 2
0.5859	Remote Similarity	NPD6083	Phase 2
0.5859	Remote Similarity	NPD7902	Approved
0.5851	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4518	Approved
0.5851	Remote Similarity	NPD6903	Approved
0.5849	Remote Similarity	NPD4634	Approved
0.5844	Remote Similarity	NPD3198	Approved
0.5843	Remote Similarity	NPD6930	Phase 2
0.5843	Remote Similarity	NPD6931	Approved
0.5843	Remote Similarity	NPD7332	Phase 2
0.5843	Remote Similarity	NPD7514	Phase 3
0.5816	Remote Similarity	NPD5695	Phase 3
0.581	Remote Similarity	NPD6686	Approved
0.58	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7638	Approved
0.5797	Remote Similarity	NPD4265	Approved
0.5795	Remote Similarity	NPD7145	Approved
0.5794	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4137	Phase 3
0.5783	Remote Similarity	NPD6923	Approved
0.5783	Remote Similarity	NPD6922	Approved
0.5778	Remote Similarity	NPD6902	Approved
0.5778	Remote Similarity	NPD857	Phase 3
0.5747	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6933	Approved
0.573	Remote Similarity	NPD4195	Approved
0.5729	Remote Similarity	NPD4096	Approved
0.5728	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD4747	Approved
0.5714	Remote Similarity	NPD7144	Approved
0.5714	Remote Similarity	NPD7143	Approved
0.5714	Remote Similarity	NPD287	Approved
0.5714	Remote Similarity	NPD5697	Approved
0.5699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD4058	Approved
0.5684	Remote Similarity	NPD5737	Approved
0.5684	Remote Similarity	NPD6672	Approved
0.5676	Remote Similarity	NPD7500	Approved
0.5673	Remote Similarity	NPD1237	Approved
0.567	Remote Similarity	NPD5281	Approved
0.567	Remote Similarity	NPD5284	Approved
0.566	Remote Similarity	NPD6011	Approved
0.566	Remote Similarity	NPD6881	Approved
0.566	Remote Similarity	NPD5128	Approved
0.566	Remote Similarity	NPD5168	Approved
0.566	Remote Similarity	NPD4730	Approved
0.566	Remote Similarity	NPD4729	Approved
0.566	Remote Similarity	NPD6899	Approved
0.5658	Remote Similarity	NPD4219	Approved
0.5652	Remote Similarity	NPD6695	Phase 3
0.5647	Remote Similarity	NPD5276	Approved
0.5647	Remote Similarity	NPD7151	Approved
0.5647	Remote Similarity	NPD7152	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