NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.22
Volume:	294.55
LogP:	1.577
LogD:	1.936
LogS:	-2.816
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.217
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.595
MDCK Permeability:	2.361541919526644e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	70.94275665283203%
Volume Distribution (VD):	0.994
Pgp-substrate:	21.868967056274414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.105
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	5.017
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.534
Carcinogencity:	0.023
Eye Corrosion:	0.951
Eye Irritation:	0.908
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC236588

Natural Product ID:	NPC236588
*Common Name:**	13,14,15,16-Tetranorlabdane-8Alpha,12,14-Triol
IUPAC Name:	(1R,2R,4aR,5R,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	OSLJXGPVHCLGHU-XFIYOXNOSA-N
Standard InCHI:	InChI=1S/C16H30O3/c1-14(11-18)7-4-8-15(2)12(14)5-9-16(3,19)13(15)6-10-17/h12-13,17-19H,4-11H2,1-3H3/t12-,13+,14-,15-,16+/m0/s1
SMILES:	OCC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCC[C@@]2(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520723
PubChem CID:	13854967
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary 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
NPO25356	Crassocephalum mannii	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[18473477]
NPO25356	Crassocephalum mannii	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18473477]
NPO25356	Crassocephalum mannii	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18473477]
NPO25356	Crassocephalum mannii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	44.0	%	PMID[493191]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	0.0	%	PMID[493191]

☑ 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 NPC236588 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	409
0.1-0.2	4403
0.2-0.3	17612
0.3-0.4	9117
0.4-0.5	5649
0.5-0.6	4034
0.6-0.7	1207
0.7-0.8	233
0.8-0.85	20
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC135438
0.8909	High Similarity	NPC471269
0.8548	High Similarity	NPC476928
0.8545	High Similarity	NPC102336
0.8545	High Similarity	NPC36002
0.8525	High Similarity	NPC260116
0.8525	High Similarity	NPC80463
0.8448	Intermediate Similarity	NPC47663
0.8413	Intermediate Similarity	NPC472741
0.8393	Intermediate Similarity	NPC53209
0.8387	Intermediate Similarity	NPC44122
0.8281	Intermediate Similarity	NPC470833
0.8281	Intermediate Similarity	NPC66407
0.8254	Intermediate Similarity	NPC139207
0.8254	Intermediate Similarity	NPC185874
0.8254	Intermediate Similarity	NPC48079
0.8197	Intermediate Similarity	NPC290791
0.8197	Intermediate Similarity	NPC292419
0.8197	Intermediate Similarity	NPC114891
0.8154	Intermediate Similarity	NPC282454
0.8136	Intermediate Similarity	NPC87296
0.8136	Intermediate Similarity	NPC215671
0.8136	Intermediate Similarity	NPC475515
0.8125	Intermediate Similarity	NPC2648
0.8125	Intermediate Similarity	NPC475893
0.8125	Intermediate Similarity	NPC474756
0.8113	Intermediate Similarity	NPC14552
0.8095	Intermediate Similarity	NPC142712
0.8065	Intermediate Similarity	NPC94897
0.8065	Intermediate Similarity	NPC281540
0.8065	Intermediate Similarity	NPC167995
0.8065	Intermediate Similarity	NPC159654
0.8065	Intermediate Similarity	NPC101128
0.8065	Intermediate Similarity	NPC118937
0.8033	Intermediate Similarity	NPC71460
0.8033	Intermediate Similarity	NPC148174
0.8033	Intermediate Similarity	NPC218585
0.8033	Intermediate Similarity	NPC185547
0.8033	Intermediate Similarity	NPC95804
0.803	Intermediate Similarity	NPC252182
0.803	Intermediate Similarity	NPC109457
0.803	Intermediate Similarity	NPC187471
0.803	Intermediate Similarity	NPC470071
0.803	Intermediate Similarity	NPC1340
0.803	Intermediate Similarity	NPC100586
0.803	Intermediate Similarity	NPC127094
0.803	Intermediate Similarity	NPC157422
0.8	Intermediate Similarity	NPC241085
0.8	Intermediate Similarity	NPC477820
0.8	Intermediate Similarity	NPC129829
0.8	Intermediate Similarity	NPC107919
0.8	Intermediate Similarity	NPC254037
0.8	Intermediate Similarity	NPC470830
0.8	Intermediate Similarity	NPC299948
0.8	Intermediate Similarity	NPC95958
0.8	Intermediate Similarity	NPC210323
0.7969	Intermediate Similarity	NPC204233
0.7969	Intermediate Similarity	NPC269077
0.7969	Intermediate Similarity	NPC253303
0.7969	Intermediate Similarity	NPC475884
0.7969	Intermediate Similarity	NPC473230
0.7969	Intermediate Similarity	NPC63190
0.7937	Intermediate Similarity	NPC473276
0.7937	Intermediate Similarity	NPC41577
0.7937	Intermediate Similarity	NPC2728
0.7937	Intermediate Similarity	NPC208198
0.7937	Intermediate Similarity	NPC11555
0.7937	Intermediate Similarity	NPC472946
0.7937	Intermediate Similarity	NPC60837
0.7937	Intermediate Similarity	NPC282619
0.7937	Intermediate Similarity	NPC258595
0.7937	Intermediate Similarity	NPC172613
0.7937	Intermediate Similarity	NPC474380
0.791	Intermediate Similarity	NPC253805
0.7903	Intermediate Similarity	NPC236099
0.7903	Intermediate Similarity	NPC209686
0.7903	Intermediate Similarity	NPC249078
0.7879	Intermediate Similarity	NPC232925
0.7879	Intermediate Similarity	NPC251201
0.7879	Intermediate Similarity	NPC231945
0.7879	Intermediate Similarity	NPC63588
0.7879	Intermediate Similarity	NPC192192
0.7857	Intermediate Similarity	NPC307022
0.7846	Intermediate Similarity	NPC244790
0.7846	Intermediate Similarity	NPC469987
0.7833	Intermediate Similarity	NPC476735
0.7818	Intermediate Similarity	NPC316035
0.7797	Intermediate Similarity	NPC3025
0.7794	Intermediate Similarity	NPC475793
0.7794	Intermediate Similarity	NPC237510
0.7794	Intermediate Similarity	NPC304499
0.7794	Intermediate Similarity	NPC10476
0.7794	Intermediate Similarity	NPC192501
0.7794	Intermediate Similarity	NPC228994
0.7794	Intermediate Similarity	NPC475458
0.7778	Intermediate Similarity	NPC69149
0.7778	Intermediate Similarity	NPC147343
0.7778	Intermediate Similarity	NPC198540
0.7778	Intermediate Similarity	NPC176309
0.7778	Intermediate Similarity	NPC287550
0.7778	Intermediate Similarity	NPC144650
0.7778	Intermediate Similarity	NPC84030
0.7778	Intermediate Similarity	NPC223468
0.7761	Intermediate Similarity	NPC473279
0.7761	Intermediate Similarity	NPC167706
0.7761	Intermediate Similarity	NPC478103
0.7761	Intermediate Similarity	NPC131506
0.7761	Intermediate Similarity	NPC157777
0.7761	Intermediate Similarity	NPC195530
0.7705	Intermediate Similarity	NPC185116
0.7692	Intermediate Similarity	NPC472984
0.7692	Intermediate Similarity	NPC41542
0.7681	Intermediate Similarity	NPC158208
0.7681	Intermediate Similarity	NPC196136
0.7681	Intermediate Similarity	NPC317242
0.7681	Intermediate Similarity	NPC472952
0.7681	Intermediate Similarity	NPC3403
0.7681	Intermediate Similarity	NPC472950
0.7681	Intermediate Similarity	NPC243027
0.7656	Intermediate Similarity	NPC190827
0.7656	Intermediate Similarity	NPC243469
0.7656	Intermediate Similarity	NPC230047
0.7656	Intermediate Similarity	NPC475943
0.7656	Intermediate Similarity	NPC19311
0.7647	Intermediate Similarity	NPC470610
0.7647	Intermediate Similarity	NPC153719
0.7647	Intermediate Similarity	NPC95165
0.7647	Intermediate Similarity	NPC472341
0.7647	Intermediate Similarity	NPC473238
0.7647	Intermediate Similarity	NPC81759
0.7576	Intermediate Similarity	NPC276616
0.7576	Intermediate Similarity	NPC245795
0.7571	Intermediate Similarity	NPC63958
0.7571	Intermediate Similarity	NPC163597
0.7541	Intermediate Similarity	NPC474769
0.7541	Intermediate Similarity	NPC189290
0.7538	Intermediate Similarity	NPC473929
0.7536	Intermediate Similarity	NPC470151
0.7536	Intermediate Similarity	NPC476366
0.7536	Intermediate Similarity	NPC48795
0.7536	Intermediate Similarity	NPC201048
0.7536	Intermediate Similarity	NPC477508
0.75	Intermediate Similarity	NPC68656
0.75	Intermediate Similarity	NPC164022
0.75	Intermediate Similarity	NPC127283
0.75	Intermediate Similarity	NPC89310
0.75	Intermediate Similarity	NPC8004
0.7465	Intermediate Similarity	NPC105208
0.7465	Intermediate Similarity	NPC474574
0.7465	Intermediate Similarity	NPC128951
0.7465	Intermediate Similarity	NPC475031
0.7465	Intermediate Similarity	NPC64081
0.7465	Intermediate Similarity	NPC185915
0.7465	Intermediate Similarity	NPC476233
0.7465	Intermediate Similarity	NPC302578
0.7465	Intermediate Similarity	NPC192046
0.7465	Intermediate Similarity	NPC477227
0.7465	Intermediate Similarity	NPC169994
0.7463	Intermediate Similarity	NPC213178
0.7463	Intermediate Similarity	NPC131892
0.7463	Intermediate Similarity	NPC327728
0.7463	Intermediate Similarity	NPC6120
0.7463	Intermediate Similarity	NPC9942
0.7458	Intermediate Similarity	NPC32222
0.7458	Intermediate Similarity	NPC202146
0.7429	Intermediate Similarity	NPC231680
0.7429	Intermediate Similarity	NPC91387
0.7429	Intermediate Similarity	NPC270306
0.7424	Intermediate Similarity	NPC88454
0.7424	Intermediate Similarity	NPC101307
0.7424	Intermediate Similarity	NPC117607
0.7391	Intermediate Similarity	NPC282905
0.7391	Intermediate Similarity	NPC68426
0.7391	Intermediate Similarity	NPC211009
0.7391	Intermediate Similarity	NPC232112
0.7391	Intermediate Similarity	NPC477229
0.7385	Intermediate Similarity	NPC64123
0.7361	Intermediate Similarity	NPC301707
0.7361	Intermediate Similarity	NPC147993
0.7361	Intermediate Similarity	NPC471769
0.7361	Intermediate Similarity	NPC18857
0.7361	Intermediate Similarity	NPC67657
0.7353	Intermediate Similarity	NPC92801
0.7353	Intermediate Similarity	NPC45296
0.7353	Intermediate Similarity	NPC283316
0.7333	Intermediate Similarity	NPC300189
0.7324	Intermediate Similarity	NPC107963
0.7324	Intermediate Similarity	NPC86305
0.7324	Intermediate Similarity	NPC470749
0.7324	Intermediate Similarity	NPC14112
0.7324	Intermediate Similarity	NPC91573
0.7324	Intermediate Similarity	NPC470145
0.7324	Intermediate Similarity	NPC106432
0.7321	Intermediate Similarity	NPC314087
0.7313	Intermediate Similarity	NPC478228
0.7302	Intermediate Similarity	NPC204173
0.7286	Intermediate Similarity	NPC472503
0.7286	Intermediate Similarity	NPC168511
0.7286	Intermediate Similarity	NPC159325
0.7286	Intermediate Similarity	NPC476736

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 NPC236588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	4387
0.2-0.3	3049
0.3-0.4	770
0.4-0.5	251
0.5-0.6	183
0.6-0.7	41
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD384	Approved
0.7778	Intermediate Similarity	NPD385	Approved
0.7612	Intermediate Similarity	NPD4787	Phase 1
0.7463	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD388	Approved
0.7273	Intermediate Similarity	NPD386	Approved
0.7246	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD371	Approved
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7183	Intermediate Similarity	NPD3703	Phase 2
0.7162	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD6117	Approved
0.7059	Intermediate Similarity	NPD5360	Phase 3
0.7059	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3698	Phase 2
0.6892	Remote Similarity	NPD6697	Approved
0.6892	Remote Similarity	NPD6118	Approved
0.6892	Remote Similarity	NPD6114	Approved
0.6892	Remote Similarity	NPD6115	Approved
0.6857	Remote Similarity	NPD4244	Approved
0.6857	Remote Similarity	NPD4789	Approved
0.6857	Remote Similarity	NPD4245	Approved
0.6812	Remote Similarity	NPD6705	Phase 1
0.68	Remote Similarity	NPD7645	Phase 2
0.6761	Remote Similarity	NPD4758	Discontinued
0.6711	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD3671	Phase 1
0.6622	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD1810	Approved
0.6575	Remote Similarity	NPD1811	Approved
0.6522	Remote Similarity	NPD4224	Phase 2
0.6494	Remote Similarity	NPD4748	Discontinued
0.6486	Remote Similarity	NPD3702	Approved
0.6486	Remote Similarity	NPD6942	Approved
0.6486	Remote Similarity	NPD7339	Approved
0.6351	Remote Similarity	NPD6924	Approved
0.6351	Remote Similarity	NPD6926	Approved
0.6316	Remote Similarity	NPD367	Approved
0.6296	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7509	Discontinued
0.6234	Remote Similarity	NPD5364	Discontinued
0.622	Remote Similarity	NPD3618	Phase 1
0.6184	Remote Similarity	NPD6933	Approved
0.6164	Remote Similarity	NPD2686	Approved
0.6164	Remote Similarity	NPD2687	Approved
0.6164	Remote Similarity	NPD2254	Approved
0.6163	Remote Similarity	NPD4202	Approved
0.6125	Remote Similarity	NPD3667	Approved
0.6081	Remote Similarity	NPD6081	Approved
0.6081	Remote Similarity	NPD4243	Approved
0.6049	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD5328	Approved
0.5976	Remote Similarity	NPD4786	Approved
0.5952	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.593	Remote Similarity	NPD6700	Approved
0.593	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4784	Approved
0.5921	Remote Similarity	NPD4785	Approved
0.5889	Remote Similarity	NPD4755	Approved
0.5875	Remote Similarity	NPD6931	Approved
0.5875	Remote Similarity	NPD6930	Phase 2
0.5867	Remote Similarity	NPD5777	Approved
0.5867	Remote Similarity	NPD7151	Approved
0.5867	Remote Similarity	NPD7150	Approved
0.5867	Remote Similarity	NPD7152	Approved
0.5862	Remote Similarity	NPD6079	Approved
0.5862	Remote Similarity	NPD6703	Approved
0.5862	Remote Similarity	NPD6702	Approved
0.5862	Remote Similarity	NPD8035	Phase 2
0.5862	Remote Similarity	NPD7515	Phase 2
0.5862	Remote Similarity	NPD8034	Phase 2
0.5854	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3669	Approved
0.5844	Remote Similarity	NPD8264	Approved
0.5844	Remote Similarity	NPD4190	Phase 3
0.5844	Remote Similarity	NPD5275	Approved
0.5811	Remote Similarity	NPD6922	Approved
0.5811	Remote Similarity	NPD6923	Approved
0.5795	Remote Similarity	NPD8171	Discontinued
0.5783	Remote Similarity	NPD3133	Approved
0.5783	Remote Similarity	NPD3665	Phase 1
0.5783	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD4700	Approved
0.5761	Remote Similarity	NPD5286	Approved
0.5761	Remote Similarity	NPD4696	Approved
0.5761	Remote Similarity	NPD5285	Approved
0.575	Remote Similarity	NPD4195	Approved
0.575	Remote Similarity	NPD6929	Approved
0.5733	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD7143	Approved
0.5733	Remote Similarity	NPD7144	Approved
0.5714	Remote Similarity	NPD368	Approved
0.5699	Remote Similarity	NPD5223	Approved
0.5696	Remote Similarity	NPD6932	Approved
0.5663	Remote Similarity	NPD6695	Phase 3
0.5647	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5226	Approved
0.5638	Remote Similarity	NPD5225	Approved
0.5638	Remote Similarity	NPD5224	Approved
0.5638	Remote Similarity	NPD4633	Approved
0.5638	Remote Similarity	NPD5211	Phase 2
0.5632	Remote Similarity	NPD4753	Phase 2
0.5625	Remote Similarity	NPD3617	Approved
0.5625	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4697	Phase 3
0.5604	Remote Similarity	NPD5221	Approved
0.5604	Remote Similarity	NPD5222	Approved
0.5604	Remote Similarity	NPD5220	Clinical (unspecified phase)

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