NPASS Compound

Structure

NPC329852 OpenBabel07101718182D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.6644 2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6644 -1.2023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -2.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1517 -1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4614 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 1.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 1.0065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 -0.0568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 1.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 -0.7683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 -0.8251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4614 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0289 1.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0289 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9032 1.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 -0.6572 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9032 -0.2935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -1.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5366 2.0661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9238 -1.4796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 13 1 1 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	4.785
LogD:	4.144
LogS:	-4.326
# Rotatable Bonds:	1
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	5.074
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	2.721096097957343e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	95.71871948242188%
Volume Distribution (VD):	0.805
Pgp-substrate:	1.334523320198059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.11
CYP1A2-substrate:	0.449
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.262
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.768
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	2.945
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.571
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC329852

Natural Product ID:	NPC329852
*Common Name:**	Brassicolide
IUPAC Name:	(1S,5E,9E)-2-(2-hydroxypropan-2-yl)-5,9-dimethyl-15-oxabicyclo[11.2.1]hexadeca-5,9,13(16)-trien-14-one
Synonyms:	Brassicolide
Standard InCHIKey:	VIPUZYFCPBOJJF-UNIGNBCPSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-7-5-8-15(2)11-12-17(20(3,4)22)18-13-16(10-6-9-14)19(21)23-18/h8-9,13,17-18,22H,5-7,10-12H2,1-4H3/b14-9+,15-8+/t17?,18-/m0/s1
SMILES:	C/C/1=CCC/C(=C/CCC2=C[C@@H](C(CC1)C(O)(C)C)OC2=O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481650
PubChem CID:	21775543
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO24464	Nephthea brassica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[10579864]
NPO24464	Nephthea brassica	Species	Nephtheidae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.44	ug ml-1	PMID[475909]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.4	ug ml-1	PMID[475909]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.81	ug ml-1	PMID[475909]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[475909]

☑ 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 NPC329852 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	171
0.1-0.2	1136
0.2-0.3	5763
0.3-0.4	15743
0.4-0.5	9574
0.5-0.6	6387
0.6-0.7	3224
0.7-0.8	671
0.8-0.85	21
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC474758
0.8947	High Similarity	NPC325031
0.8767	High Similarity	NPC294434
0.8767	High Similarity	NPC259599
0.8767	High Similarity	NPC15499
0.8767	High Similarity	NPC117746
0.8442	Intermediate Similarity	NPC178277
0.8421	Intermediate Similarity	NPC57744
0.8356	Intermediate Similarity	NPC67183
0.8333	Intermediate Similarity	NPC276290
0.8312	Intermediate Similarity	NPC108816
0.8312	Intermediate Similarity	NPC128276
0.8312	Intermediate Similarity	NPC93763
0.8312	Intermediate Similarity	NPC267231
0.8228	Intermediate Similarity	NPC471325
0.8219	Intermediate Similarity	NPC265574
0.8214	Intermediate Similarity	NPC473448
0.8194	Intermediate Similarity	NPC472266
0.8182	Intermediate Similarity	NPC320630
0.8182	Intermediate Similarity	NPC116177
0.8182	Intermediate Similarity	NPC7563
0.8171	Intermediate Similarity	NPC469483
0.8169	Intermediate Similarity	NPC470688
0.8148	Intermediate Similarity	NPC82297
0.8148	Intermediate Similarity	NPC476804
0.8125	Intermediate Similarity	NPC474291
0.8082	Intermediate Similarity	NPC470256
0.8072	Intermediate Similarity	NPC160138
0.8056	Intermediate Similarity	NPC248125
0.8052	Intermediate Similarity	NPC123360
0.8026	Intermediate Similarity	NPC476355
0.8025	Intermediate Similarity	NPC169575
0.8025	Intermediate Similarity	NPC40746
0.8025	Intermediate Similarity	NPC250315
0.8	Intermediate Similarity	NPC78677
0.8	Intermediate Similarity	NPC67076
0.8	Intermediate Similarity	NPC319163
0.8	Intermediate Similarity	NPC42470
0.8	Intermediate Similarity	NPC59994
0.8	Intermediate Similarity	NPC163003
0.7976	Intermediate Similarity	NPC476805
0.7975	Intermediate Similarity	NPC469617
0.7975	Intermediate Similarity	NPC98557
0.7975	Intermediate Similarity	NPC167881
0.7952	Intermediate Similarity	NPC305475
0.7952	Intermediate Similarity	NPC261721
0.7952	Intermediate Similarity	NPC475461
0.7945	Intermediate Similarity	NPC194871
0.7927	Intermediate Similarity	NPC474865
0.7907	Intermediate Similarity	NPC177037
0.7907	Intermediate Similarity	NPC472814
0.7901	Intermediate Similarity	NPC85772
0.7901	Intermediate Similarity	NPC26624
0.7887	Intermediate Similarity	NPC68110
0.7887	Intermediate Similarity	NPC217940
0.7875	Intermediate Similarity	NPC233377
0.7857	Intermediate Similarity	NPC45957
0.7857	Intermediate Similarity	NPC312561
0.7857	Intermediate Similarity	NPC471657
0.7848	Intermediate Similarity	NPC471465
0.7848	Intermediate Similarity	NPC196653
0.7838	Intermediate Similarity	NPC218477
0.7838	Intermediate Similarity	NPC310210
0.7831	Intermediate Similarity	NPC470755
0.7831	Intermediate Similarity	NPC86316
0.7831	Intermediate Similarity	NPC106416
0.7831	Intermediate Similarity	NPC255307
0.7831	Intermediate Similarity	NPC261380
0.7831	Intermediate Similarity	NPC215364
0.7831	Intermediate Similarity	NPC65661
0.7821	Intermediate Similarity	NPC469880
0.7821	Intermediate Similarity	NPC68819
0.7816	Intermediate Similarity	NPC139692
0.7816	Intermediate Similarity	NPC115021
0.7805	Intermediate Similarity	NPC116543
0.7805	Intermediate Similarity	NPC475947
0.7805	Intermediate Similarity	NPC473390
0.7805	Intermediate Similarity	NPC44261
0.7805	Intermediate Similarity	NPC311070
0.7805	Intermediate Similarity	NPC131669
0.7805	Intermediate Similarity	NPC59097
0.7792	Intermediate Similarity	NPC140287
0.7792	Intermediate Similarity	NPC476590
0.7792	Intermediate Similarity	NPC114727
0.7792	Intermediate Similarity	NPC470686
0.7791	Intermediate Similarity	NPC475855
0.7791	Intermediate Similarity	NPC144133
0.7791	Intermediate Similarity	NPC179394
0.7778	Intermediate Similarity	NPC141810
0.7778	Intermediate Similarity	NPC52861
0.7778	Intermediate Similarity	NPC24417
0.7765	Intermediate Similarity	NPC260343
0.7765	Intermediate Similarity	NPC476803
0.7763	Intermediate Similarity	NPC257618
0.7763	Intermediate Similarity	NPC129665
0.7763	Intermediate Similarity	NPC472254
0.775	Intermediate Similarity	NPC470239
0.775	Intermediate Similarity	NPC89128
0.775	Intermediate Similarity	NPC270126
0.775	Intermediate Similarity	NPC470244
0.775	Intermediate Similarity	NPC617
0.7746	Intermediate Similarity	NPC151648
0.7738	Intermediate Similarity	NPC150755
0.7738	Intermediate Similarity	NPC122502
0.7733	Intermediate Similarity	NPC476591
0.7733	Intermediate Similarity	NPC151481
0.7733	Intermediate Similarity	NPC88877
0.7733	Intermediate Similarity	NPC232812
0.7733	Intermediate Similarity	NPC101622
0.7727	Intermediate Similarity	NPC477131
0.7727	Intermediate Similarity	NPC469632
0.7722	Intermediate Similarity	NPC141789
0.7722	Intermediate Similarity	NPC476439
0.7722	Intermediate Similarity	NPC262747
0.7722	Intermediate Similarity	NPC474760
0.7722	Intermediate Similarity	NPC68156
0.7722	Intermediate Similarity	NPC187568
0.7722	Intermediate Similarity	NPC10572
0.7722	Intermediate Similarity	NPC97516
0.7722	Intermediate Similarity	NPC476028
0.7722	Intermediate Similarity	NPC41780
0.7722	Intermediate Similarity	NPC171204
0.7711	Intermediate Similarity	NPC158756
0.7711	Intermediate Similarity	NPC191476
0.7711	Intermediate Similarity	NPC141193
0.7711	Intermediate Similarity	NPC156485
0.7711	Intermediate Similarity	NPC196487
0.7711	Intermediate Similarity	NPC70424
0.7711	Intermediate Similarity	NPC114979
0.7711	Intermediate Similarity	NPC31086
0.7711	Intermediate Similarity	NPC243618
0.7711	Intermediate Similarity	NPC96259
0.7711	Intermediate Similarity	NPC14575
0.7701	Intermediate Similarity	NPC111114
0.7701	Intermediate Similarity	NPC261607
0.7701	Intermediate Similarity	NPC300312
0.7692	Intermediate Similarity	NPC68624
0.7683	Intermediate Similarity	NPC35556
0.7683	Intermediate Similarity	NPC229825
0.7683	Intermediate Similarity	NPC173609
0.7683	Intermediate Similarity	NPC89555
0.7674	Intermediate Similarity	NPC295312
0.7674	Intermediate Similarity	NPC5509
0.7674	Intermediate Similarity	NPC212598
0.7674	Intermediate Similarity	NPC174342
0.7662	Intermediate Similarity	NPC269206
0.7662	Intermediate Similarity	NPC58956
0.7662	Intermediate Similarity	NPC295633
0.7654	Intermediate Similarity	NPC281132
0.764	Intermediate Similarity	NPC304886
0.7639	Intermediate Similarity	NPC155849
0.7632	Intermediate Similarity	NPC318766
0.7632	Intermediate Similarity	NPC469660
0.7632	Intermediate Similarity	NPC37929
0.7632	Intermediate Similarity	NPC64234
0.7632	Intermediate Similarity	NPC4299
0.7625	Intermediate Similarity	NPC474816
0.7625	Intermediate Similarity	NPC192006
0.7625	Intermediate Similarity	NPC299235
0.7625	Intermediate Similarity	NPC471220
0.7625	Intermediate Similarity	NPC253749
0.7625	Intermediate Similarity	NPC209135
0.7619	Intermediate Similarity	NPC165162
0.7619	Intermediate Similarity	NPC125290
0.7614	Intermediate Similarity	NPC228451
0.7614	Intermediate Similarity	NPC475838
0.7614	Intermediate Similarity	NPC125674
0.76	Intermediate Similarity	NPC474823
0.7595	Intermediate Similarity	NPC235906
0.7595	Intermediate Similarity	NPC476317
0.7595	Intermediate Similarity	NPC27205
0.759	Intermediate Similarity	NPC193198
0.759	Intermediate Similarity	NPC472377
0.759	Intermediate Similarity	NPC16488
0.759	Intermediate Similarity	NPC474809
0.759	Intermediate Similarity	NPC53867
0.759	Intermediate Similarity	NPC42476
0.7586	Intermediate Similarity	NPC51486
0.7586	Intermediate Similarity	NPC232426
0.7586	Intermediate Similarity	NPC469368
0.7586	Intermediate Similarity	NPC281942
0.7568	Intermediate Similarity	NPC191233
0.7564	Intermediate Similarity	NPC160540
0.7561	Intermediate Similarity	NPC281949
0.7561	Intermediate Similarity	NPC112868
0.7561	Intermediate Similarity	NPC475944
0.7561	Intermediate Similarity	NPC25684
0.7561	Intermediate Similarity	NPC301477
0.7558	Intermediate Similarity	NPC475819
0.7558	Intermediate Similarity	NPC469653
0.7558	Intermediate Similarity	NPC475906
0.7558	Intermediate Similarity	NPC469631
0.7558	Intermediate Similarity	NPC471047
0.7558	Intermediate Similarity	NPC469628
0.7556	Intermediate Similarity	NPC242848
0.7556	Intermediate Similarity	NPC134072
0.7556	Intermediate Similarity	NPC234993
0.7534	Intermediate Similarity	NPC34883
0.7532	Intermediate Similarity	NPC316185
0.7532	Intermediate Similarity	NPC84038

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 NPC329852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1732
0.2-0.3	3989
0.3-0.4	2315
0.4-0.5	607
0.5-0.6	288
0.6-0.7	59
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
0.7917	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5209	Approved
0.7229	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4820	Approved
0.7229	Intermediate Similarity	NPD4819	Approved
0.7229	Intermediate Similarity	NPD4822	Approved
0.7229	Intermediate Similarity	NPD4821	Approved
0.7209	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6698	Approved
0.7191	Intermediate Similarity	NPD5785	Approved
0.7191	Intermediate Similarity	NPD46	Approved
0.7176	Intermediate Similarity	NPD7154	Phase 3
0.7093	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4225	Approved
0.7011	Intermediate Similarity	NPD5363	Approved
0.7011	Intermediate Similarity	NPD1694	Approved
0.7011	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7838	Discovery
0.6988	Remote Similarity	NPD4268	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4271	Approved
0.6977	Remote Similarity	NPD5362	Discontinued
0.6889	Remote Similarity	NPD1695	Approved
0.6869	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6435	Approved
0.6842	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD6686	Approved
0.6782	Remote Similarity	NPD5331	Approved
0.6782	Remote Similarity	NPD5332	Approved
0.6771	Remote Similarity	NPD7639	Approved
0.6771	Remote Similarity	NPD7640	Approved
0.6744	Remote Similarity	NPD5369	Approved
0.6744	Remote Similarity	NPD4790	Discontinued
0.6742	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6628	Remote Similarity	NPD5368	Approved
0.6628	Remote Similarity	NPD4252	Approved
0.6627	Remote Similarity	NPD8039	Approved
0.6579	Remote Similarity	NPD368	Approved
0.6571	Remote Similarity	NPD6927	Phase 3
0.6559	Remote Similarity	NPD7637	Suspended
0.6556	Remote Similarity	NPD5786	Approved
0.6531	Remote Similarity	NPD5344	Discontinued
0.6526	Remote Similarity	NPD5695	Phase 3
0.6489	Remote Similarity	NPD5778	Approved
0.6489	Remote Similarity	NPD5779	Approved
0.6456	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD6648	Approved
0.6392	Remote Similarity	NPD6083	Phase 2
0.6392	Remote Similarity	NPD6084	Phase 2
0.6383	Remote Similarity	NPD7983	Approved
0.6381	Remote Similarity	NPD6053	Discontinued
0.6374	Remote Similarity	NPD7146	Approved
0.6374	Remote Similarity	NPD5330	Approved
0.6374	Remote Similarity	NPD6684	Approved
0.6374	Remote Similarity	NPD7521	Approved
0.6374	Remote Similarity	NPD7334	Approved
0.6374	Remote Similarity	NPD6409	Approved
0.6344	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6101	Approved
0.6327	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD7115	Discovery
0.6279	Remote Similarity	NPD4756	Discovery
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD6647	Phase 2
0.6237	Remote Similarity	NPD6903	Approved
0.6237	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6110	Phase 1
0.6214	Remote Similarity	NPD5697	Approved
0.6211	Remote Similarity	NPD6411	Approved
0.6211	Remote Similarity	NPD5693	Phase 1
0.6203	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6051	Approved
0.6154	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD3665	Phase 1
0.6154	Remote Similarity	NPD3133	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6146	Remote Similarity	NPD6399	Phase 3
0.6139	Remote Similarity	NPD7632	Discontinued
0.6125	Remote Similarity	NPD7341	Phase 2
0.6122	Remote Similarity	NPD7839	Suspended
0.6117	Remote Similarity	NPD7128	Approved
0.6117	Remote Similarity	NPD6675	Approved
0.6117	Remote Similarity	NPD6402	Approved
0.6117	Remote Similarity	NPD5739	Approved
0.6095	Remote Similarity	NPD6012	Approved
0.6095	Remote Similarity	NPD6014	Approved
0.6095	Remote Similarity	NPD6013	Approved
0.6087	Remote Similarity	NPD1696	Phase 3
0.6064	Remote Similarity	NPD6672	Approved
0.6064	Remote Similarity	NPD5737	Approved
0.6061	Remote Similarity	NPD7902	Approved
0.6058	Remote Similarity	NPD5701	Approved
0.6056	Remote Similarity	NPD3173	Approved
0.6042	Remote Similarity	NPD7515	Phase 2
0.6038	Remote Similarity	NPD6883	Approved
0.6038	Remote Similarity	NPD7290	Approved
0.6038	Remote Similarity	NPD7102	Approved
0.6022	Remote Similarity	NPD4519	Discontinued
0.6022	Remote Similarity	NPD4623	Approved
0.6022	Remote Similarity	NPD3618	Phase 1
0.6022	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD8130	Phase 1
0.5981	Remote Similarity	NPD6650	Approved
0.5981	Remote Similarity	NPD2204	Approved
0.5981	Remote Similarity	NPD6847	Approved
0.5981	Remote Similarity	NPD6869	Approved
0.5981	Remote Similarity	NPD6649	Approved
0.5981	Remote Similarity	NPD6617	Approved
0.5976	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6109	Phase 1
0.5962	Remote Similarity	NPD4211	Phase 1
0.5957	Remote Similarity	NPD3573	Approved
0.5949	Remote Similarity	NPD4192	Approved
0.5949	Remote Similarity	NPD4191	Approved
0.5949	Remote Similarity	NPD4193	Approved
0.5949	Remote Similarity	NPD4194	Approved
0.5946	Remote Similarity	NPD3172	Approved
0.5943	Remote Similarity	NPD6373	Approved
0.5943	Remote Similarity	NPD6372	Approved
0.5934	Remote Similarity	NPD4221	Approved
0.5934	Remote Similarity	NPD3667	Approved
0.5934	Remote Similarity	NPD4223	Phase 3
0.5926	Remote Similarity	NPD8297	Approved
0.5926	Remote Similarity	NPD6882	Approved
0.5915	Remote Similarity	NPD5343	Approved
0.5905	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5208	Approved
0.5889	Remote Similarity	NPD7332	Phase 2
0.5889	Remote Similarity	NPD4695	Discontinued
0.5889	Remote Similarity	NPD7514	Phase 3
0.5876	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD5284	Approved
0.5876	Remote Similarity	NPD6079	Approved
0.5876	Remote Similarity	NPD5281	Approved
0.587	Remote Similarity	NPD6695	Phase 3
0.5867	Remote Similarity	NPD3194	Approved
0.5867	Remote Similarity	NPD3195	Phase 2
0.5867	Remote Similarity	NPD4266	Approved
0.5867	Remote Similarity	NPD3196	Approved
0.5862	Remote Similarity	NPD7507	Approved
0.5859	Remote Similarity	NPD4629	Approved
0.5859	Remote Similarity	NPD5210	Approved
0.5857	Remote Similarity	NPD4222	Approved
0.5851	Remote Similarity	NPD6422	Discontinued
0.5851	Remote Similarity	NPD5690	Phase 2
0.5843	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5328	Approved
0.5833	Remote Similarity	NPD6080	Approved
0.5833	Remote Similarity	NPD6673	Approved
0.5833	Remote Similarity	NPD6904	Approved
0.5825	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4202	Approved
0.5806	Remote Similarity	NPD4786	Approved
0.5806	Remote Similarity	NPD4197	Approved
0.5806	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7327	Approved
0.5804	Remote Similarity	NPD7328	Approved
0.58	Remote Similarity	NPD4228	Discovery
0.58	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD342	Phase 1
0.5784	Remote Similarity	NPD5285	Approved
0.5784	Remote Similarity	NPD5286	Approved
0.5784	Remote Similarity	NPD4696	Approved
0.5778	Remote Similarity	NPD4195	Approved
0.5773	Remote Similarity	NPD5207	Approved
0.5773	Remote Similarity	NPD5692	Phase 3
0.5766	Remote Similarity	NPD6274	Approved
0.5761	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7900	Approved
0.5752	Remote Similarity	NPD7516	Approved
0.5747	Remote Similarity	NPD6924	Approved
0.5747	Remote Similarity	NPD6926	Approved
0.5745	Remote Similarity	NPD5329	Approved
0.5743	Remote Similarity	NPD4755	Approved
0.573	Remote Similarity	NPD6932	Approved
0.573	Remote Similarity	NPD5776	Phase 2
0.573	Remote Similarity	NPD6925	Approved
0.5714	Remote Similarity	NPD6930	Phase 2

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