NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.1
Volume:	176.711
LogP:	1.55
LogD:	1.548
LogS:	-1.707
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.177
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.563
MDCK Permeability:	2.0314093490014784e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.37
Human Intestinal Absorption (HIA):	0.503
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957
Plasma Protein Binding (PPB):	48.35472869873047%
Volume Distribution (VD):	0.996
Pgp-substrate:	41.876502990722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	6.743
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.69
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.95
Carcinogencity:	0.894
Eye Corrosion:	0.957
Eye Irritation:	0.99
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: NPC242722

Natural Product ID:	NPC242722
*Common Name:**	Isotsaokoin
IUPAC Name:	(3aS,7R,7aR)-7-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carbaldehyde
Synonyms:	Isotsaokoin
Standard InCHIKey:	CBXWAUXGOHHAIT-OPRDCNLKSA-N
Standard InCHI:	InChI=1S/C10H14O2/c11-6-7-4-5-10(12)9-3-1-2-8(7)9/h4,6,8-10,12H,1-3,5H2/t8-,9-,10-/m1/s1
SMILES:	C1C[C@@H]2C(=CC[C@H]([C@@H]2C1)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470663
PubChem CID:	10397152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO40539	Amomum tsao-ko	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165158]
NPO40539	Amomum tsao-ko	Species	Zingiberaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31244142]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	2.0	mm	PMID[564028]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	1.5	mm	PMID[564028]

☑ 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 NPC242722 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	163
0.1-0.2	1227
0.2-0.3	7231
0.3-0.4	16424
0.4-0.5	8967
0.5-0.6	6191
0.6-0.7	2293
0.7-0.8	194
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC136150
0.8125	Intermediate Similarity	NPC119229
0.8101	Intermediate Similarity	NPC181195
0.8101	Intermediate Similarity	NPC261125
0.7952	Intermediate Similarity	NPC36350
0.7831	Intermediate Similarity	NPC470812
0.7821	Intermediate Similarity	NPC472256
0.7778	Intermediate Similarity	NPC45495
0.775	Intermediate Similarity	NPC80088
0.775	Intermediate Similarity	NPC475994
0.775	Intermediate Similarity	NPC253561
0.7722	Intermediate Similarity	NPC470525
0.7722	Intermediate Similarity	NPC469646
0.7711	Intermediate Similarity	NPC476082
0.7711	Intermediate Similarity	NPC278648
0.7711	Intermediate Similarity	NPC470165
0.7701	Intermediate Similarity	NPC191684
0.7701	Intermediate Similarity	NPC183283
0.7674	Intermediate Similarity	NPC328539
0.7654	Intermediate Similarity	NPC7232
0.7647	Intermediate Similarity	NPC118648
0.7647	Intermediate Similarity	NPC232156
0.7647	Intermediate Similarity	NPC183736
0.7647	Intermediate Similarity	NPC145879
0.7647	Intermediate Similarity	NPC474732
0.7647	Intermediate Similarity	NPC474733
0.7647	Intermediate Similarity	NPC475022
0.7647	Intermediate Similarity	NPC474778
0.7647	Intermediate Similarity	NPC222613
0.7647	Intermediate Similarity	NPC31564
0.7625	Intermediate Similarity	NPC276769
0.7619	Intermediate Similarity	NPC7927
0.7619	Intermediate Similarity	NPC230527
0.7595	Intermediate Similarity	NPC114236
0.759	Intermediate Similarity	NPC151519
0.7586	Intermediate Similarity	NPC275740
0.7586	Intermediate Similarity	NPC123912
0.7586	Intermediate Similarity	NPC86319
0.7586	Intermediate Similarity	NPC186688
0.7558	Intermediate Similarity	NPC475740
0.7558	Intermediate Similarity	NPC58063
0.7531	Intermediate Similarity	NPC62336
0.7529	Intermediate Similarity	NPC470574
0.7529	Intermediate Similarity	NPC469948
0.7529	Intermediate Similarity	NPC202868
0.7528	Intermediate Similarity	NPC250575
0.75	Intermediate Similarity	NPC64600
0.75	Intermediate Similarity	NPC215481
0.75	Intermediate Similarity	NPC474748
0.7473	Intermediate Similarity	NPC192428
0.7471	Intermediate Similarity	NPC143767
0.7471	Intermediate Similarity	NPC474925
0.7471	Intermediate Similarity	NPC206060
0.7471	Intermediate Similarity	NPC473229
0.7471	Intermediate Similarity	NPC471722
0.7471	Intermediate Similarity	NPC131470
0.7468	Intermediate Similarity	NPC215050
0.7442	Intermediate Similarity	NPC94755
0.7442	Intermediate Similarity	NPC20688
0.7442	Intermediate Similarity	NPC327115
0.7439	Intermediate Similarity	NPC19900
0.7416	Intermediate Similarity	NPC185936
0.7416	Intermediate Similarity	NPC99380
0.7416	Intermediate Similarity	NPC168027
0.7412	Intermediate Similarity	NPC59453
0.7412	Intermediate Similarity	NPC473246
0.7412	Intermediate Similarity	NPC161423
0.7412	Intermediate Similarity	NPC472265
0.7412	Intermediate Similarity	NPC321187
0.7412	Intermediate Similarity	NPC227064
0.7412	Intermediate Similarity	NPC329043
0.7412	Intermediate Similarity	NPC214043
0.7412	Intermediate Similarity	NPC58841
0.7412	Intermediate Similarity	NPC85774
0.7412	Intermediate Similarity	NPC221758
0.7403	Intermediate Similarity	NPC250928
0.7403	Intermediate Similarity	NPC10758
0.7386	Intermediate Similarity	NPC31985
0.7386	Intermediate Similarity	NPC268406
0.7386	Intermediate Similarity	NPC119416
0.7386	Intermediate Similarity	NPC1015
0.7386	Intermediate Similarity	NPC26959
0.7381	Intermediate Similarity	NPC158411
0.7381	Intermediate Similarity	NPC38796
0.7375	Intermediate Similarity	NPC474011
0.7349	Intermediate Similarity	NPC472301
0.7349	Intermediate Similarity	NPC472478
0.7349	Intermediate Similarity	NPC271104
0.7342	Intermediate Similarity	NPC261316
0.7342	Intermediate Similarity	NPC186042
0.7342	Intermediate Similarity	NPC49737
0.7333	Intermediate Similarity	NPC109414
0.7333	Intermediate Similarity	NPC474304
0.7333	Intermediate Similarity	NPC109305
0.7333	Intermediate Similarity	NPC474329
0.7333	Intermediate Similarity	NPC69454
0.7312	Intermediate Similarity	NPC114274
0.7303	Intermediate Similarity	NPC48010
0.7303	Intermediate Similarity	NPC477711
0.7294	Intermediate Similarity	NPC52609
0.7294	Intermediate Similarity	NPC1761
0.7294	Intermediate Similarity	NPC62214
0.7284	Intermediate Similarity	NPC263582
0.7283	Intermediate Similarity	NPC471463
0.7273	Intermediate Similarity	NPC158778
0.7273	Intermediate Similarity	NPC193843
0.7273	Intermediate Similarity	NPC249889
0.7273	Intermediate Similarity	NPC477710
0.7273	Intermediate Similarity	NPC53911
0.7253	Intermediate Similarity	NPC166906
0.725	Intermediate Similarity	NPC102313
0.725	Intermediate Similarity	NPC199316
0.7241	Intermediate Similarity	NPC472974
0.7241	Intermediate Similarity	NPC51014
0.7241	Intermediate Similarity	NPC155011
0.7241	Intermediate Similarity	NPC72133
0.7234	Intermediate Similarity	NPC112167
0.7229	Intermediate Similarity	NPC152061
0.7229	Intermediate Similarity	NPC229204
0.7229	Intermediate Similarity	NPC470429
0.7229	Intermediate Similarity	NPC472490
0.7229	Intermediate Similarity	NPC308038
0.7222	Intermediate Similarity	NPC63748
0.7222	Intermediate Similarity	NPC131872
0.7222	Intermediate Similarity	NPC272746
0.7222	Intermediate Similarity	NPC172101
0.7209	Intermediate Similarity	NPC33913
0.7209	Intermediate Similarity	NPC237712
0.7195	Intermediate Similarity	NPC470428
0.7195	Intermediate Similarity	NPC471061
0.7195	Intermediate Similarity	NPC197659
0.7191	Intermediate Similarity	NPC310236
0.7191	Intermediate Similarity	NPC472983
0.7191	Intermediate Similarity	NPC473999
0.7191	Intermediate Similarity	NPC309603
0.7191	Intermediate Similarity	NPC472973
0.7191	Intermediate Similarity	NPC477943
0.7179	Intermediate Similarity	NPC469914
0.7176	Intermediate Similarity	NPC470813
0.7176	Intermediate Similarity	NPC93590
0.7174	Intermediate Similarity	NPC279313
0.7174	Intermediate Similarity	NPC472932
0.7174	Intermediate Similarity	NPC259286
0.7174	Intermediate Similarity	NPC470016
0.7174	Intermediate Similarity	NPC317586
0.7174	Intermediate Similarity	NPC473170
0.7159	Intermediate Similarity	NPC93778
0.7159	Intermediate Similarity	NPC136548
0.7159	Intermediate Similarity	NPC475772
0.7159	Intermediate Similarity	NPC141292
0.7159	Intermediate Similarity	NPC472324
0.7143	Intermediate Similarity	NPC134826
0.7143	Intermediate Similarity	NPC474736
0.7143	Intermediate Similarity	NPC2482
0.7143	Intermediate Similarity	NPC472930
0.7143	Intermediate Similarity	NPC471514
0.7128	Intermediate Similarity	NPC222011
0.7128	Intermediate Similarity	NPC197386
0.7126	Intermediate Similarity	NPC476426
0.7126	Intermediate Similarity	NPC474853
0.7126	Intermediate Similarity	NPC197823
0.7126	Intermediate Similarity	NPC179006
0.7125	Intermediate Similarity	NPC300940
0.7111	Intermediate Similarity	NPC85173
0.7111	Intermediate Similarity	NPC126993
0.7108	Intermediate Similarity	NPC207772
0.7108	Intermediate Similarity	NPC59436
0.7108	Intermediate Similarity	NPC476949
0.7108	Intermediate Similarity	NPC172066
0.7108	Intermediate Similarity	NPC178852
0.7097	Intermediate Similarity	NPC305483
0.7097	Intermediate Similarity	NPC5532
0.7097	Intermediate Similarity	NPC61369
0.7097	Intermediate Similarity	NPC471039
0.7097	Intermediate Similarity	NPC249954
0.7097	Intermediate Similarity	NPC328162
0.7097	Intermediate Similarity	NPC96859
0.7097	Intermediate Similarity	NPC469545
0.7093	Intermediate Similarity	NPC307258
0.7093	Intermediate Similarity	NPC110150
0.7093	Intermediate Similarity	NPC105173
0.7093	Intermediate Similarity	NPC470948
0.7093	Intermediate Similarity	NPC66764
0.7089	Intermediate Similarity	NPC173321
0.7083	Intermediate Similarity	NPC473424
0.7079	Intermediate Similarity	NPC328313
0.7079	Intermediate Similarity	NPC474854
0.7079	Intermediate Similarity	NPC471724
0.7079	Intermediate Similarity	NPC292491
0.7079	Intermediate Similarity	NPC310752
0.7079	Intermediate Similarity	NPC474677
0.7073	Intermediate Similarity	NPC472959
0.7073	Intermediate Similarity	NPC186554
0.7073	Intermediate Similarity	NPC76966
0.7071	Intermediate Similarity	NPC177064
0.7065	Intermediate Similarity	NPC472976
0.7065	Intermediate Similarity	NPC471207
0.7065	Intermediate Similarity	NPC472977
0.7065	Intermediate Similarity	NPC292793
0.7065	Intermediate Similarity	NPC196485

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 NPC242722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1872
0.2-0.3	4278
0.3-0.4	2050
0.4-0.5	450
0.5-0.6	225
0.6-0.7	118
0.7-0.8	9
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
0.7614	Intermediate Similarity	NPD6079	Approved
0.759	Intermediate Similarity	NPD3667	Approved
0.7586	Intermediate Similarity	NPD5328	Approved
0.7473	Intermediate Similarity	NPD4697	Phase 3
0.7442	Intermediate Similarity	NPD3618	Phase 1
0.7412	Intermediate Similarity	NPD3133	Approved
0.7412	Intermediate Similarity	NPD3665	Phase 1
0.7412	Intermediate Similarity	NPD3666	Approved
0.7412	Intermediate Similarity	NPD4786	Approved
0.7283	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5221	Approved
0.7283	Intermediate Similarity	NPD5222	Approved
0.7241	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD5173	Approved
0.7053	Intermediate Similarity	NPD5285	Approved
0.7053	Intermediate Similarity	NPD4696	Approved
0.7053	Intermediate Similarity	NPD5286	Approved
0.7021	Intermediate Similarity	NPD4755	Approved
0.7013	Intermediate Similarity	NPD7331	Phase 2
0.6979	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD4202	Approved
0.6907	Remote Similarity	NPD5224	Approved
0.6907	Remote Similarity	NPD5225	Approved
0.6907	Remote Similarity	NPD4633	Approved
0.6907	Remote Similarity	NPD5226	Approved
0.6907	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD4700	Approved
0.6837	Remote Similarity	NPD5174	Approved
0.6837	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD3668	Phase 3
0.6813	Remote Similarity	NPD4753	Phase 2
0.6782	Remote Similarity	NPD4223	Phase 3
0.6782	Remote Similarity	NPD4221	Approved
0.6768	Remote Similarity	NPD5141	Approved
0.6744	Remote Similarity	NPD5368	Approved
0.6744	Remote Similarity	NPD4695	Discontinued
0.6742	Remote Similarity	NPD5363	Approved
0.6742	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD4629	Approved
0.6632	Remote Similarity	NPD5210	Approved
0.6629	Remote Similarity	NPD4197	Approved
0.6596	Remote Similarity	NPD6399	Phase 3
0.6591	Remote Similarity	NPD6435	Approved
0.6569	Remote Similarity	NPD6011	Approved
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD4730	Approved
0.6569	Remote Similarity	NPD5128	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6556	Remote Similarity	NPD5329	Approved
0.6548	Remote Similarity	NPD7339	Approved
0.6548	Remote Similarity	NPD6942	Approved
0.6535	Remote Similarity	NPD4767	Approved
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD4768	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6517	Remote Similarity	NPD5362	Discontinued
0.6512	Remote Similarity	NPD3617	Approved
0.6505	Remote Similarity	NPD6013	Approved
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6012	Approved
0.6489	Remote Similarity	NPD7515	Phase 2
0.6484	Remote Similarity	NPD5205	Approved
0.6484	Remote Similarity	NPD5786	Approved
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6484	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6463	Remote Similarity	NPD4691	Approved
0.6452	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6101	Approved
0.6442	Remote Similarity	NPD5135	Approved
0.6442	Remote Similarity	NPD5250	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD5251	Approved
0.6442	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD5249	Phase 3
0.6442	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD5247	Approved
0.6442	Remote Similarity	NPD5169	Approved
0.6442	Remote Similarity	NPD5248	Approved
0.641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7320	Approved
0.6404	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD4269	Approved
0.6383	Remote Similarity	NPD5785	Approved
0.6381	Remote Similarity	NPD5215	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD6650	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6381	Remote Similarity	NPD5127	Approved
0.6381	Remote Similarity	NPD5217	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6649	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD5216	Approved
0.6364	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4252	Approved
0.6346	Remote Similarity	NPD6372	Approved
0.6346	Remote Similarity	NPD6373	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4518	Approved
0.6341	Remote Similarity	NPD4137	Phase 3
0.6333	Remote Similarity	NPD4788	Approved
0.6327	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD6083	Phase 2
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4271	Approved
0.6322	Remote Similarity	NPD4268	Approved
0.6321	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6292	Remote Similarity	NPD4790	Discontinued
0.6289	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5695	Phase 3
0.6265	Remote Similarity	NPD4747	Approved
0.6262	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4195	Approved
0.6235	Remote Similarity	NPD6924	Approved
0.6235	Remote Similarity	NPD4058	Approved
0.6235	Remote Similarity	NPD6926	Approved
0.6226	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4096	Approved
0.6204	Remote Similarity	NPD5167	Approved
0.6196	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5276	Approved
0.619	Remote Similarity	NPD7152	Approved
0.619	Remote Similarity	NPD7151	Approved
0.619	Remote Similarity	NPD7150	Approved
0.6186	Remote Similarity	NPD7748	Approved
0.618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4822	Approved
0.618	Remote Similarity	NPD4819	Approved
0.618	Remote Similarity	NPD4820	Approved
0.618	Remote Similarity	NPD4821	Approved
0.6173	Remote Similarity	NPD3704	Approved
0.617	Remote Similarity	NPD6672	Approved
0.617	Remote Similarity	NPD5737	Approved
0.6168	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6154	Remote Similarity	NPD7154	Phase 3
0.6147	Remote Similarity	NPD6868	Approved
0.6147	Remote Similarity	NPD6274	Approved
0.6146	Remote Similarity	NPD5284	Approved
0.6146	Remote Similarity	NPD5281	Approved
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6129	Remote Similarity	NPD4623	Approved
0.6129	Remote Similarity	NPD4519	Discontinued
0.61	Remote Similarity	NPD7638	Approved
0.61	Remote Similarity	NPD5696	Approved
0.6092	Remote Similarity	NPD6933	Approved
0.6091	Remote Similarity	NPD6009	Approved
0.6091	Remote Similarity	NPD6317	Approved
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6064	Remote Similarity	NPD3573	Approved
0.6058	Remote Similarity	NPD6008	Approved
0.6047	Remote Similarity	NPD4687	Approved
0.6047	Remote Similarity	NPD5733	Approved
0.6044	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD6314	Approved
0.6036	Remote Similarity	NPD6313	Approved
0.6036	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD7902	Approved
0.5982	Remote Similarity	NPD7101	Approved
0.5982	Remote Similarity	NPD7100	Approved
0.5977	Remote Similarity	NPD8264	Approved
0.5976	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7115	Discovery

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