NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	3.063
LogD:	3.335
LogS:	-3.839
# 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:	4.35
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.456
MDCK Permeability:	2.3842105292715132e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.166
20% Bioavailability (F20%):	0.526
30% Bioavailability (F30%):	0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	82.14807891845703%
Volume Distribution (VD):	0.852
Pgp-substrate:	8.620840072631836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.436
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.181
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	6.355
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.583
Drug-inuced Liver Injury (DILI):	0.175
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.323
Skin Sensitization:	0.933
Carcinogencity:	0.705
Eye Corrosion:	0.929
Eye Irritation:	0.901
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC253561

Natural Product ID:	NPC253561
*Common Name:**	Canangaterpene Iii
IUPAC Name:	(4aS,5R,8S,8aR)-5-hydroxy-5-methyl-8-propan-2-yl-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carbaldehyde
Synonyms:
Standard InCHIKey:	FHFKLFYRFFKTRP-ZQDZILKHSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-10(2)12-6-7-15(3,17)14-5-4-11(9-16)8-13(12)14/h8-10,12-14,17H,4-7H2,1-3H3/t12-,13-,14-,15+/m0/s1
SMILES:	O=CC1=C[C@@H]2[C@H](CC1)[C@](C)(O)CC[C@H]2C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262198
PubChem CID:	90676284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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	=	19.2	%	PMID[528849]
NPT2	Others	Unspecified	Inhibition	=	29.9	%	PMID[528849]
NPT2	Others	Unspecified	Inhibition	=	35.8	%	PMID[528849]
NPT2	Others	Unspecified	Inhibition	=	50.8	%	PMID[528849]
NPT2	Others	Unspecified	Inhibition	=	66.3	%	PMID[528849]
NPT2	Others	Unspecified	Inhibition	=	26.2	%	PMID[528849]
NPT27	Others	Unspecified	Activity	>	80.3	%	PMID[528849]

☑ 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 NPC253561 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	1167
0.2-0.3	5323
0.3-0.4	14117
0.4-0.5	10832
0.5-0.6	6835
0.6-0.7	3510
0.7-0.8	697
0.8-0.85	39
0.85-0.9	8
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80088
0.96	High Similarity	NPC119229
0.9467	High Similarity	NPC472301
0.9189	High Similarity	NPC76966
0.9189	High Similarity	NPC186554
0.8947	High Similarity	NPC207772
0.875	High Similarity	NPC470812
0.8684	High Similarity	NPC472305
0.8625	High Similarity	NPC64600
0.8571	High Similarity	NPC34110
0.8571	High Similarity	NPC197659
0.8571	High Similarity	NPC257666
0.8571	High Similarity	NPC266193
0.8554	High Similarity	NPC473229
0.8554	High Similarity	NPC206060
0.8481	Intermediate Similarity	NPC476809
0.8452	Intermediate Similarity	NPC472983
0.8442	Intermediate Similarity	NPC151622
0.8442	Intermediate Similarity	NPC7629
0.8415	Intermediate Similarity	NPC70685
0.8395	Intermediate Similarity	NPC297398
0.8375	Intermediate Similarity	NPC473217
0.8353	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC474925
0.8333	Intermediate Similarity	NPC470428
0.8313	Intermediate Similarity	NPC179591
0.8272	Intermediate Similarity	NPC470813
0.825	Intermediate Similarity	NPC172013
0.825	Intermediate Similarity	NPC469637
0.8228	Intermediate Similarity	NPC62336
0.8228	Intermediate Similarity	NPC19443
0.8228	Intermediate Similarity	NPC476949
0.8228	Intermediate Similarity	NPC59436
0.8205	Intermediate Similarity	NPC470525
0.8205	Intermediate Similarity	NPC263582
0.8182	Intermediate Similarity	NPC78527
0.8171	Intermediate Similarity	NPC307258
0.8148	Intermediate Similarity	NPC473420
0.8148	Intermediate Similarity	NPC90055
0.8148	Intermediate Similarity	NPC226068
0.8125	Intermediate Similarity	NPC308038
0.8125	Intermediate Similarity	NPC470429
0.8125	Intermediate Similarity	NPC283789
0.8095	Intermediate Similarity	NPC472974
0.8095	Intermediate Similarity	NPC95594
0.8095	Intermediate Similarity	NPC477579
0.8095	Intermediate Similarity	NPC235341
0.8095	Intermediate Similarity	NPC94755
0.8072	Intermediate Similarity	NPC251170
0.8052	Intermediate Similarity	NPC35656
0.8049	Intermediate Similarity	NPC93590
0.8046	Intermediate Similarity	NPC99380
0.8025	Intermediate Similarity	NPC2482
0.8025	Intermediate Similarity	NPC271104
0.8025	Intermediate Similarity	NPC471514
0.8023	Intermediate Similarity	NPC119416
0.8023	Intermediate Similarity	NPC472973
0.8	Intermediate Similarity	NPC275494
0.8	Intermediate Similarity	NPC178852
0.8	Intermediate Similarity	NPC471409
0.7976	Intermediate Similarity	NPC470574
0.7975	Intermediate Similarity	NPC250621
0.7949	Intermediate Similarity	NPC470299
0.7931	Intermediate Similarity	NPC183283
0.7931	Intermediate Similarity	NPC134321
0.7931	Intermediate Similarity	NPC128672
0.7931	Intermediate Similarity	NPC85173
0.7927	Intermediate Similarity	NPC116797
0.7927	Intermediate Similarity	NPC121984
0.7917	Intermediate Similarity	NPC282694
0.7917	Intermediate Similarity	NPC79576
0.7917	Intermediate Similarity	NPC194208
0.7907	Intermediate Similarity	NPC48107
0.7907	Intermediate Similarity	NPC328539
0.7907	Intermediate Similarity	NPC472802
0.7907	Intermediate Similarity	NPC158778
0.7907	Intermediate Similarity	NPC471722
0.7901	Intermediate Similarity	NPC281138
0.7901	Intermediate Similarity	NPC170394
0.7901	Intermediate Similarity	NPC152061
0.7889	Intermediate Similarity	NPC5532
0.7889	Intermediate Similarity	NPC469545
0.7889	Intermediate Similarity	NPC61369
0.7882	Intermediate Similarity	NPC73038
0.7882	Intermediate Similarity	NPC158393
0.7882	Intermediate Similarity	NPC472986
0.7882	Intermediate Similarity	NPC472985
0.7882	Intermediate Similarity	NPC72133
0.7875	Intermediate Similarity	NPC97377
0.7867	Intermediate Similarity	NPC4370
0.7867	Intermediate Similarity	NPC263161
0.7867	Intermediate Similarity	NPC290350
0.7857	Intermediate Similarity	NPC476412
0.7848	Intermediate Similarity	NPC476795
0.7848	Intermediate Similarity	NPC114236
0.7841	Intermediate Similarity	NPC172101
0.7841	Intermediate Similarity	NPC472975
0.7841	Intermediate Similarity	NPC272746
0.7841	Intermediate Similarity	NPC472978
0.7841	Intermediate Similarity	NPC116726
0.7831	Intermediate Similarity	NPC103486
0.7831	Intermediate Similarity	NPC48362
0.7821	Intermediate Similarity	NPC247586
0.7816	Intermediate Similarity	NPC275740
0.7816	Intermediate Similarity	NPC184663
0.7816	Intermediate Similarity	NPC86319
0.7805	Intermediate Similarity	NPC148685
0.7805	Intermediate Similarity	NPC824
0.7805	Intermediate Similarity	NPC233352
0.7805	Intermediate Similarity	NPC104120
0.7805	Intermediate Similarity	NPC157895
0.7805	Intermediate Similarity	NPC108955
0.7805	Intermediate Similarity	NPC138492
0.7805	Intermediate Similarity	NPC472478
0.7791	Intermediate Similarity	NPC475740
0.7791	Intermediate Similarity	NPC475772
0.7791	Intermediate Similarity	NPC141292
0.7778	Intermediate Similarity	NPC476808
0.7778	Intermediate Similarity	NPC321514
0.7778	Intermediate Similarity	NPC74410
0.7778	Intermediate Similarity	NPC476245
0.7778	Intermediate Similarity	NPC189485
0.7765	Intermediate Similarity	NPC133954
0.7763	Intermediate Similarity	NPC155198
0.7753	Intermediate Similarity	NPC134826
0.775	Intermediate Similarity	NPC242722
0.775	Intermediate Similarity	NPC215481
0.775	Intermediate Similarity	NPC180886
0.7738	Intermediate Similarity	NPC110150
0.7738	Intermediate Similarity	NPC251475
0.7738	Intermediate Similarity	NPC470165
0.7738	Intermediate Similarity	NPC169941
0.7738	Intermediate Similarity	NPC66764
0.7727	Intermediate Similarity	NPC474209
0.7727	Intermediate Similarity	NPC328141
0.7727	Intermediate Similarity	NPC126993
0.7727	Intermediate Similarity	NPC472476
0.7727	Intermediate Similarity	NPC475823
0.7722	Intermediate Similarity	NPC22134
0.7711	Intermediate Similarity	NPC327002
0.7711	Intermediate Similarity	NPC55869
0.7711	Intermediate Similarity	NPC278459
0.7701	Intermediate Similarity	NPC131470
0.7701	Intermediate Similarity	NPC474677
0.7701	Intermediate Similarity	NPC471791
0.7701	Intermediate Similarity	NPC471793
0.7701	Intermediate Similarity	NPC471724
0.7701	Intermediate Similarity	NPC292491
0.7701	Intermediate Similarity	NPC310752
0.7701	Intermediate Similarity	NPC143767
0.7701	Intermediate Similarity	NPC104560
0.7692	Intermediate Similarity	NPC242992
0.7692	Intermediate Similarity	NPC164022
0.7692	Intermediate Similarity	NPC474562
0.7692	Intermediate Similarity	NPC84790
0.7692	Intermediate Similarity	NPC23954
0.7692	Intermediate Similarity	NPC192428
0.7683	Intermediate Similarity	NPC472490
0.7674	Intermediate Similarity	NPC475862
0.7674	Intermediate Similarity	NPC476043
0.7674	Intermediate Similarity	NPC213412
0.7674	Intermediate Similarity	NPC6979
0.7674	Intermediate Similarity	NPC474732
0.7674	Intermediate Similarity	NPC474733
0.7674	Intermediate Similarity	NPC94666
0.7674	Intermediate Similarity	NPC473226
0.7674	Intermediate Similarity	NPC31564
0.7674	Intermediate Similarity	NPC325594
0.7674	Intermediate Similarity	NPC474778
0.7674	Intermediate Similarity	NPC74363
0.7674	Intermediate Similarity	NPC194417
0.7674	Intermediate Similarity	NPC145879
0.7667	Intermediate Similarity	NPC472977
0.7667	Intermediate Similarity	NPC472976
0.7667	Intermediate Similarity	NPC23170
0.7667	Intermediate Similarity	NPC196227
0.7667	Intermediate Similarity	NPC299100
0.7667	Intermediate Similarity	NPC471207
0.7667	Intermediate Similarity	NPC471040
0.7667	Intermediate Similarity	NPC103527
0.7662	Intermediate Similarity	NPC469914
0.7654	Intermediate Similarity	NPC203403
0.7654	Intermediate Similarity	NPC325946
0.7654	Intermediate Similarity	NPC165711
0.7654	Intermediate Similarity	NPC74995
0.7647	Intermediate Similarity	NPC237712
0.7647	Intermediate Similarity	NPC85774
0.7647	Intermediate Similarity	NPC30486
0.7647	Intermediate Similarity	NPC214043
0.7647	Intermediate Similarity	NPC329043
0.7647	Intermediate Similarity	NPC321187
0.7647	Intermediate Similarity	NPC40687
0.7647	Intermediate Similarity	NPC58841
0.7647	Intermediate Similarity	NPC473246
0.7647	Intermediate Similarity	NPC161423
0.7647	Intermediate Similarity	NPC227064
0.764	Intermediate Similarity	NPC233455
0.764	Intermediate Similarity	NPC131872
0.764	Intermediate Similarity	NPC185936
0.764	Intermediate Similarity	NPC65120

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 NPC253561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1643
0.2-0.3	3949
0.3-0.4	2373
0.4-0.5	629
0.5-0.6	210
0.6-0.7	157
0.7-0.8	35
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
0.8095	Intermediate Similarity	NPD3618	Phase 1
0.7841	Intermediate Similarity	NPD6079	Approved
0.7816	Intermediate Similarity	NPD5328	Approved
0.7753	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD4697	Phase 3
0.7674	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD7515	Phase 2
0.7619	Intermediate Similarity	NPD4221	Approved
0.7619	Intermediate Similarity	NPD3667	Approved
0.7619	Intermediate Similarity	NPD4223	Phase 3
0.759	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5221	Approved
0.7473	Intermediate Similarity	NPD7748	Approved
0.7471	Intermediate Similarity	NPD5690	Phase 2
0.7447	Intermediate Similarity	NPD4696	Approved
0.7447	Intermediate Similarity	NPD5285	Approved
0.7447	Intermediate Similarity	NPD5286	Approved
0.7442	Intermediate Similarity	NPD4786	Approved
0.7442	Intermediate Similarity	NPD4197	Approved
0.7419	Intermediate Similarity	NPD4755	Approved
0.7419	Intermediate Similarity	NPD5173	Approved
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7386	Intermediate Similarity	NPD3573	Approved
0.7368	Intermediate Similarity	NPD5223	Approved
0.7356	Intermediate Similarity	NPD5329	Approved
0.7292	Intermediate Similarity	NPD5224	Approved
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7292	Intermediate Similarity	NPD5225	Approved
0.7292	Intermediate Similarity	NPD4633	Approved
0.7292	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD7331	Phase 2
0.7273	Intermediate Similarity	NPD4138	Approved
0.7273	Intermediate Similarity	NPD4688	Approved
0.7273	Intermediate Similarity	NPD5279	Phase 3
0.7273	Intermediate Similarity	NPD4690	Approved
0.7273	Intermediate Similarity	NPD4519	Discontinued
0.7273	Intermediate Similarity	NPD4693	Phase 3
0.7273	Intermediate Similarity	NPD5205	Approved
0.7273	Intermediate Similarity	NPD4694	Approved
0.7273	Intermediate Similarity	NPD4689	Approved
0.7273	Intermediate Similarity	NPD4623	Approved
0.7263	Intermediate Similarity	NPD4700	Approved
0.7234	Intermediate Similarity	NPD7902	Approved
0.7216	Intermediate Similarity	NPD5175	Approved
0.7216	Intermediate Similarity	NPD5174	Approved
0.7204	Intermediate Similarity	NPD4629	Approved
0.7204	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7143	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7059	Intermediate Similarity	NPD4195	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD4754	Approved
0.7021	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD5697	Approved
0.6966	Remote Similarity	NPD1694	Approved
0.6966	Remote Similarity	NPD1696	Phase 3
0.6932	Remote Similarity	NPD4788	Approved
0.6931	Remote Similarity	NPD6011	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD4729	Approved
0.6931	Remote Similarity	NPD4730	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6931	Remote Similarity	NPD5128	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7900	Approved
0.6914	Remote Similarity	NPD4691	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD4768	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.69	Remote Similarity	NPD4767	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD7521	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD6012	Approved
0.6863	Remote Similarity	NPD6014	Approved
0.686	Remote Similarity	NPD7645	Phase 2
0.6832	Remote Similarity	NPD5701	Approved
0.6818	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6399	Phase 3
0.6804	Remote Similarity	NPD5696	Approved
0.6796	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5250	Approved
0.6796	Remote Similarity	NPD5247	Approved
0.6796	Remote Similarity	NPD4634	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6796	Remote Similarity	NPD5169	Approved
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD5251	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD5135	Approved
0.6796	Remote Similarity	NPD5248	Approved
0.6796	Remote Similarity	NPD5249	Phase 3
0.679	Remote Similarity	NPD4137	Phase 3
0.6782	Remote Similarity	NPD7525	Registered
0.6778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD5168	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6903	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6731	Remote Similarity	NPD5215	Approved
0.6731	Remote Similarity	NPD5127	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD5216	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD5217	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6707	Remote Similarity	NPD4747	Approved
0.6706	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4139	Approved
0.6705	Remote Similarity	NPD4692	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6633	Remote Similarity	NPD7638	Approved
0.6632	Remote Similarity	NPD5133	Approved
0.6604	Remote Similarity	NPD4632	Approved
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6942	Approved
0.6588	Remote Similarity	NPD7339	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD7640	Approved
0.6562	Remote Similarity	NPD6001	Approved
0.6559	Remote Similarity	NPD5208	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6542	Remote Similarity	NPD5167	Approved
0.6538	Remote Similarity	NPD368	Approved
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD6673	Approved
0.6489	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD6080	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD5733	Approved
0.6471	Remote Similarity	NPD4687	Approved
0.6465	Remote Similarity	NPD5290	Discontinued
0.6465	Remote Similarity	NPD4225	Approved
0.6456	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5091	Approved
0.6429	Remote Similarity	NPD5276	Approved
0.6429	Remote Similarity	NPD7614	Phase 1
0.6429	Remote Similarity	NPD4243	Approved
0.6422	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD6009	Approved
0.6422	Remote Similarity	NPD6317	Approved
0.6421	Remote Similarity	NPD5207	Approved
0.6421	Remote Similarity	NPD5692	Phase 3
0.6408	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.6364	Remote Similarity	NPD287	Approved
0.6364	Remote Similarity	NPD6313	Approved
0.6354	Remote Similarity	NPD6050	Approved
0.6354	Remote Similarity	NPD5694	Approved
0.6354	Remote Similarity	NPD8035	Phase 2
0.6354	Remote Similarity	NPD8034	Phase 2
0.6354	Remote Similarity	NPD6411	Approved
0.6354	Remote Similarity	NPD5693	Phase 1
0.6344	Remote Similarity	NPD6098	Approved
0.633	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD7101	Approved
0.6306	Remote Similarity	NPD7100	Approved
0.6289	Remote Similarity	NPD5778	Approved
0.6289	Remote Similarity	NPD5779	Approved
0.6279	Remote Similarity	NPD4785	Approved
0.6279	Remote Similarity	NPD4784	Approved
0.6279	Remote Similarity	NPD6924	Approved
0.6279	Remote Similarity	NPD6926	Approved
0.6265	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD6319	Approved
0.6238	Remote Similarity	NPD6404	Discontinued

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