NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	2.822
LogD:	2.962
LogS:	-2.79
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	4.281
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.593
MDCK Permeability:	2.1253466911730357e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.378

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	83.16600799560547%
Volume Distribution (VD):	0.68
Pgp-substrate:	15.217269897460938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.219
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.266
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	9.932
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.596
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.936
Carcinogencity:	0.283
Eye Corrosion:	0.884
Eye Irritation:	0.655
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC181195

Natural Product ID:	NPC181195
*Common Name:**	10Beta-Hydroxyisodauc-6-En-14-Al
IUPAC Name:	(3R,3aR,8S,8aS)-8-hydroxy-8a-methyl-3-propan-2-yl-2,3,3a,6,7,8-hexahydro-1H-azulene-5-carbaldehyde
Synonyms:
Standard InCHIKey:	VBTLMTQHIPAVNS-QPSCCSFWSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-10(2)12-6-7-15(3)13(12)8-11(9-16)4-5-14(15)17/h8-10,12-14,17H,4-7H2,1-3H3/t12-,13+,14+,15+/m1/s1
SMILES:	CC(C)[C@H]1CC[C@@]2(C)[C@H]1C=C(CC[C@@H]2O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262199
PubChem CID:	46849806
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
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	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
Others	7

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	-4.4	%	PMID[520464]
NPT2	Others	Unspecified	Inhibition	=	9.2	%	PMID[520464]
NPT2	Others	Unspecified	Inhibition	=	14.7	%	PMID[520464]
NPT2	Others	Unspecified	Inhibition	=	37.7	%	PMID[520464]
NPT2	Others	Unspecified	Inhibition	=	58.8	%	PMID[520464]
NPT2	Others	Unspecified	Inhibition	=	57.5	%	PMID[520464]
NPT27	Others	Unspecified	Activity	>	80.3	%	PMID[520464]

☑ 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 NPC181195 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	175
0.1-0.2	1357
0.2-0.3	7420
0.3-0.4	15805
0.4-0.5	8284
0.5-0.6	6534
0.6-0.7	2696
0.7-0.8	402
0.8-0.85	17
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261125
0.9324	High Similarity	NPC215481
0.8571	High Similarity	NPC469646
0.8462	Intermediate Similarity	NPC276769
0.8452	Intermediate Similarity	NPC477710
0.8256	Intermediate Similarity	NPC477711
0.8205	Intermediate Similarity	NPC474011
0.8193	Intermediate Similarity	NPC7927
0.8193	Intermediate Similarity	NPC230527
0.8182	Intermediate Similarity	NPC300940
0.8171	Intermediate Similarity	NPC133844
0.8148	Intermediate Similarity	NPC164218
0.8101	Intermediate Similarity	NPC242722
0.8072	Intermediate Similarity	NPC470165
0.8049	Intermediate Similarity	NPC136150
0.8026	Intermediate Similarity	NPC10758
0.8026	Intermediate Similarity	NPC61702
0.8026	Intermediate Similarity	NPC250928
0.8026	Intermediate Similarity	NPC162867
0.8025	Intermediate Similarity	NPC229204
0.7976	Intermediate Similarity	NPC470812
0.7975	Intermediate Similarity	NPC77501
0.7975	Intermediate Similarity	NPC472256
0.7931	Intermediate Similarity	NPC123912
0.7931	Intermediate Similarity	NPC232747
0.7931	Intermediate Similarity	NPC41217
0.7927	Intermediate Similarity	NPC45495
0.7882	Intermediate Similarity	NPC36350
0.7875	Intermediate Similarity	NPC472959
0.7857	Intermediate Similarity	NPC474748
0.7857	Intermediate Similarity	NPC278648
0.7857	Intermediate Similarity	NPC476082
0.7841	Intermediate Similarity	NPC2946
0.7841	Intermediate Similarity	NPC183283
0.7841	Intermediate Similarity	NPC191684
0.7821	Intermediate Similarity	NPC469737
0.7816	Intermediate Similarity	NPC328539
0.7805	Intermediate Similarity	NPC7232
0.7791	Intermediate Similarity	NPC232156
0.7778	Intermediate Similarity	NPC211279
0.7765	Intermediate Similarity	NPC85774
0.7765	Intermediate Similarity	NPC473246
0.7765	Intermediate Similarity	NPC214043
0.775	Intermediate Similarity	NPC251435
0.775	Intermediate Similarity	NPC263698
0.775	Intermediate Similarity	NPC114236
0.7733	Intermediate Similarity	NPC474304
0.7733	Intermediate Similarity	NPC474329
0.7727	Intermediate Similarity	NPC275740
0.7727	Intermediate Similarity	NPC86319
0.7727	Intermediate Similarity	NPC170775
0.7711	Intermediate Similarity	NPC471656
0.7683	Intermediate Similarity	NPC207186
0.7683	Intermediate Similarity	NPC62336
0.7674	Intermediate Similarity	NPC469948
0.7674	Intermediate Similarity	NPC202868
0.7674	Intermediate Similarity	NPC142649
0.7667	Intermediate Similarity	NPC125180
0.7667	Intermediate Similarity	NPC250575
0.7662	Intermediate Similarity	NPC167527
0.766	Intermediate Similarity	NPC237190
0.7654	Intermediate Similarity	NPC470525
0.7654	Intermediate Similarity	NPC226242
0.7647	Intermediate Similarity	NPC62214
0.7625	Intermediate Similarity	NPC102313
0.7625	Intermediate Similarity	NPC472966
0.7625	Intermediate Similarity	NPC199316
0.7625	Intermediate Similarity	NPC469691
0.7625	Intermediate Similarity	NPC167049
0.7614	Intermediate Similarity	NPC131470
0.7614	Intermediate Similarity	NPC143767
0.7609	Intermediate Similarity	NPC192428
0.759	Intermediate Similarity	NPC136033
0.759	Intermediate Similarity	NPC471890
0.759	Intermediate Similarity	NPC84185
0.759	Intermediate Similarity	NPC66677
0.7586	Intermediate Similarity	NPC474732
0.7586	Intermediate Similarity	NPC31564
0.7586	Intermediate Similarity	NPC474733
0.7586	Intermediate Similarity	NPC145879
0.7586	Intermediate Similarity	NPC94755
0.7586	Intermediate Similarity	NPC474778
0.7586	Intermediate Similarity	NPC327115
0.7561	Intermediate Similarity	NPC86917
0.7561	Intermediate Similarity	NPC197659
0.7558	Intermediate Similarity	NPC237712
0.7558	Intermediate Similarity	NPC161423
0.7558	Intermediate Similarity	NPC58841
0.7558	Intermediate Similarity	NPC227064
0.7558	Intermediate Similarity	NPC321187
0.7558	Intermediate Similarity	NPC329043
0.7556	Intermediate Similarity	NPC168027
0.7556	Intermediate Similarity	NPC185936
0.7553	Intermediate Similarity	NPC112167
0.7532	Intermediate Similarity	NPC136813
0.7531	Intermediate Similarity	NPC216791
0.7531	Intermediate Similarity	NPC469669
0.7531	Intermediate Similarity	NPC475771
0.7531	Intermediate Similarity	NPC469678
0.7528	Intermediate Similarity	NPC477943
0.7528	Intermediate Similarity	NPC186688
0.7528	Intermediate Similarity	NPC477215
0.7528	Intermediate Similarity	NPC476388
0.75	Intermediate Similarity	NPC92909
0.75	Intermediate Similarity	NPC310608
0.75	Intermediate Similarity	NPC58063
0.75	Intermediate Similarity	NPC93778
0.75	Intermediate Similarity	NPC30675
0.75	Intermediate Similarity	NPC470839
0.75	Intermediate Similarity	NPC472478
0.75	Intermediate Similarity	NPC107783
0.75	Intermediate Similarity	NPC136548
0.75	Intermediate Similarity	NPC183422
0.75	Intermediate Similarity	NPC475740
0.7473	Intermediate Similarity	NPC472930
0.7473	Intermediate Similarity	NPC477520
0.7473	Intermediate Similarity	NPC69454
0.7471	Intermediate Similarity	NPC470574
0.747	Intermediate Similarity	NPC474056
0.747	Intermediate Similarity	NPC321180
0.747	Intermediate Similarity	NPC475994
0.747	Intermediate Similarity	NPC59436
0.7468	Intermediate Similarity	NPC280256
0.7444	Intermediate Similarity	NPC126993
0.7442	Intermediate Similarity	NPC1761
0.7442	Intermediate Similarity	NPC65350
0.7442	Intermediate Similarity	NPC64600
0.7442	Intermediate Similarity	NPC52609
0.7439	Intermediate Similarity	NPC263582
0.7436	Intermediate Similarity	NPC469688
0.7419	Intermediate Similarity	NPC471039
0.7416	Intermediate Similarity	NPC474854
0.7416	Intermediate Similarity	NPC471722
0.7416	Intermediate Similarity	NPC476704
0.7416	Intermediate Similarity	NPC474925
0.7412	Intermediate Similarity	NPC90055
0.7412	Intermediate Similarity	NPC119229
0.7391	Intermediate Similarity	NPC471040
0.7391	Intermediate Similarity	NPC298919
0.7391	Intermediate Similarity	NPC90453
0.7386	Intermediate Similarity	NPC118648
0.7386	Intermediate Similarity	NPC475022
0.7386	Intermediate Similarity	NPC183736
0.7386	Intermediate Similarity	NPC6247
0.7386	Intermediate Similarity	NPC222613
0.7386	Intermediate Similarity	NPC72133
0.7381	Intermediate Similarity	NPC308038
0.7381	Intermediate Similarity	NPC469690
0.7381	Intermediate Similarity	NPC472490
0.7381	Intermediate Similarity	NPC470239
0.7381	Intermediate Similarity	NPC470244
0.7381	Intermediate Similarity	NPC152061
0.7363	Intermediate Similarity	NPC476187
0.7363	Intermediate Similarity	NPC19114
0.7363	Intermediate Similarity	NPC272746
0.7363	Intermediate Similarity	NPC63748
0.7356	Intermediate Similarity	NPC221758
0.7356	Intermediate Similarity	NPC472265
0.7356	Intermediate Similarity	NPC472957
0.7356	Intermediate Similarity	NPC82902
0.7356	Intermediate Similarity	NPC472958
0.7356	Intermediate Similarity	NPC165064
0.7356	Intermediate Similarity	NPC165287
0.7356	Intermediate Similarity	NPC475796
0.7356	Intermediate Similarity	NPC59453
0.7349	Intermediate Similarity	NPC470428
0.7342	Intermediate Similarity	NPC261398
0.7342	Intermediate Similarity	NPC469914
0.7342	Intermediate Similarity	NPC469677
0.7333	Intermediate Similarity	NPC1015
0.7333	Intermediate Similarity	NPC260573
0.7333	Intermediate Similarity	NPC309603
0.7333	Intermediate Similarity	NPC26959
0.7333	Intermediate Similarity	NPC268406
0.7333	Intermediate Similarity	NPC119416
0.7333	Intermediate Similarity	NPC31985
0.7333	Intermediate Similarity	NPC117405
0.7333	Intermediate Similarity	NPC52198
0.7333	Intermediate Similarity	NPC473999
0.7326	Intermediate Similarity	NPC470813
0.7326	Intermediate Similarity	NPC151519
0.7312	Intermediate Similarity	NPC259286
0.7312	Intermediate Similarity	NPC472932
0.7312	Intermediate Similarity	NPC279313
0.7303	Intermediate Similarity	NPC89747
0.7303	Intermediate Similarity	NPC141292
0.7303	Intermediate Similarity	NPC287079
0.7303	Intermediate Similarity	NPC475772
0.7303	Intermediate Similarity	NPC237540
0.7294	Intermediate Similarity	NPC172013
0.7294	Intermediate Similarity	NPC306095
0.7294	Intermediate Similarity	NPC471514
0.7294	Intermediate Similarity	NPC164999
0.7292	Intermediate Similarity	NPC195192
0.7292	Intermediate Similarity	NPC304738
0.7284	Intermediate Similarity	NPC275098
0.7283	Intermediate Similarity	NPC109414
0.7283	Intermediate Similarity	NPC474736
0.7283	Intermediate Similarity	NPC474807
0.7273	Intermediate Similarity	NPC474083

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 NPC181195 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2078
0.2-0.3	4277
0.3-0.4	1859
0.4-0.5	397
0.5-0.6	197
0.6-0.7	163
0.7-0.8	16
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
0.7753	Intermediate Similarity	NPD6079	Approved
0.7727	Intermediate Similarity	NPD5328	Approved
0.7609	Intermediate Similarity	NPD4697	Phase 3
0.7586	Intermediate Similarity	NPD5279	Phase 3
0.7558	Intermediate Similarity	NPD3133	Approved
0.7558	Intermediate Similarity	NPD3666	Approved
0.7558	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3618	Phase 1
0.7356	Intermediate Similarity	NPD4786	Approved
0.734	Intermediate Similarity	NPD5173	Approved
0.7326	Intermediate Similarity	NPD3667	Approved
0.7262	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7188	Intermediate Similarity	NPD5286	Approved
0.7158	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7128	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4223	Phase 3
0.7126	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD5223	Approved
0.7097	Intermediate Similarity	NPD4202	Approved
0.7093	Intermediate Similarity	NPD5368	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD5225	Approved
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.701	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.697	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD5174	Approved
0.6966	Remote Similarity	NPD4197	Approved
0.6962	Remote Similarity	NPD7331	Phase 2
0.6947	Remote Similarity	NPD4629	Approved
0.6947	Remote Similarity	NPD5210	Approved
0.6932	Remote Similarity	NPD6435	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6889	Remote Similarity	NPD5363	Approved
0.6889	Remote Similarity	NPD5329	Approved
0.6882	Remote Similarity	NPD5785	Approved
0.6854	Remote Similarity	NPD4788	Approved
0.6854	Remote Similarity	NPD5362	Discontinued
0.6835	Remote Similarity	NPD7341	Phase 2
0.6813	Remote Similarity	NPD5280	Approved
0.6813	Remote Similarity	NPD4690	Approved
0.6813	Remote Similarity	NPD4688	Approved
0.6813	Remote Similarity	NPD4689	Approved
0.6813	Remote Similarity	NPD4693	Phase 3
0.6813	Remote Similarity	NPD5205	Approved
0.6813	Remote Similarity	NPD4694	Approved
0.6813	Remote Similarity	NPD4138	Approved
0.68	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD6926	Approved
0.6786	Remote Similarity	NPD6924	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.6705	Remote Similarity	NPD4695	Discontinued
0.6699	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD5168	Approved
0.6699	Remote Similarity	NPD5128	Approved
0.6699	Remote Similarity	NPD4730	Approved
0.6699	Remote Similarity	NPD6881	Approved
0.6699	Remote Similarity	NPD4729	Approved
0.6699	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6633	Remote Similarity	NPD6084	Phase 2
0.6633	Remote Similarity	NPD6083	Phase 2
0.663	Remote Similarity	NPD6684	Approved
0.663	Remote Similarity	NPD7334	Approved
0.663	Remote Similarity	NPD7146	Approved
0.663	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5330	Approved
0.663	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD5369	Approved
0.6628	Remote Similarity	NPD6933	Approved
0.6602	Remote Similarity	NPD5701	Approved
0.6598	Remote Similarity	NPD5695	Phase 3
0.6593	Remote Similarity	NPD3668	Phase 3
0.6591	Remote Similarity	NPD4195	Approved
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD5247	Approved
0.6571	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD5135	Approved
0.6571	Remote Similarity	NPD5251	Approved
0.6562	Remote Similarity	NPD6399	Phase 3
0.6556	Remote Similarity	NPD4269	Approved
0.6556	Remote Similarity	NPD4270	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6526	Remote Similarity	NPD4096	Approved
0.6522	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7339	Approved
0.6512	Remote Similarity	NPD6942	Approved
0.6509	Remote Similarity	NPD5217	Approved
0.6509	Remote Similarity	NPD6649	Approved
0.6509	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6617	Approved
0.6509	Remote Similarity	NPD5216	Approved
0.6509	Remote Similarity	NPD5215	Approved
0.6509	Remote Similarity	NPD5127	Approved
0.6509	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD6650	Approved
0.6509	Remote Similarity	NPD6869	Approved
0.6506	Remote Similarity	NPD6922	Approved
0.6506	Remote Similarity	NPD6923	Approved
0.6489	Remote Similarity	NPD6903	Approved
0.6489	Remote Similarity	NPD5737	Approved
0.6489	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6672	Approved
0.6484	Remote Similarity	NPD5331	Approved
0.6484	Remote Similarity	NPD5332	Approved
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6373	Approved
0.6458	Remote Similarity	NPD7515	Phase 2
0.6458	Remote Similarity	NPD5281	Approved
0.6458	Remote Similarity	NPD5284	Approved
0.6458	Remote Similarity	NPD6411	Approved
0.6449	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD6882	Approved
0.6444	Remote Similarity	NPD4790	Discontinued
0.6437	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4747	Approved
0.6429	Remote Similarity	NPD7144	Approved
0.6429	Remote Similarity	NPD7143	Approved
0.6429	Remote Similarity	NPD4691	Approved
0.6404	Remote Similarity	NPD6929	Approved
0.64	Remote Similarity	NPD5696	Approved
0.6389	Remote Similarity	NPD4632	Approved
0.6374	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7150	Approved
0.6353	Remote Similarity	NPD5276	Approved
0.6353	Remote Similarity	NPD7151	Approved
0.6353	Remote Similarity	NPD7152	Approved
0.6344	Remote Similarity	NPD1696	Phase 3
0.6344	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD4822	Approved
0.6333	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD6931	Approved
0.6333	Remote Similarity	NPD6930	Phase 2
0.6333	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD7525	Registered
0.6333	Remote Similarity	NPD4819	Approved
0.6333	Remote Similarity	NPD4252	Approved
0.633	Remote Similarity	NPD5167	Approved
0.6327	Remote Similarity	NPD5282	Discontinued
0.631	Remote Similarity	NPD4137	Phase 3
0.6304	Remote Similarity	NPD7154	Phase 3
0.6292	Remote Similarity	NPD4268	Approved
0.6292	Remote Similarity	NPD4271	Approved
0.6277	Remote Similarity	NPD4519	Discontinued
0.6277	Remote Similarity	NPD4623	Approved
0.6273	Remote Similarity	NPD6274	Approved
0.6273	Remote Similarity	NPD6868	Approved
0.6264	Remote Similarity	NPD4139	Approved
0.6264	Remote Similarity	NPD4692	Approved
0.6264	Remote Similarity	NPD857	Phase 3
0.6262	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1695	Approved
0.6238	Remote Similarity	NPD7638	Approved
0.6224	Remote Similarity	NPD5133	Approved
0.622	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6317	Approved
0.6216	Remote Similarity	NPD6009	Approved
0.6207	Remote Similarity	NPD4687	Approved
0.6207	Remote Similarity	NPD4058	Approved
0.6207	Remote Similarity	NPD5733	Approved
0.6196	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5776	Phase 2
0.618	Remote Similarity	NPD6925	Approved
0.618	Remote Similarity	NPD6932	Approved
0.6176	Remote Similarity	NPD7640	Approved
0.6176	Remote Similarity	NPD7639	Approved
0.617	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7748	Approved
0.6161	Remote Similarity	NPD6313	Approved
0.6161	Remote Similarity	NPD6335	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