NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	3.088
LogD:	3.217
LogS:	-3.689
# 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:	0.76
Synthetic Accessibility Score:	4.144
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.434
MDCK Permeability:	2.6255336706526577e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	89.59854125976562%
Volume Distribution (VD):	0.659
Pgp-substrate:	10.238125801086426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.208
CYP1A2-substrate:	0.659
CYP2C19-inhibitor:	0.491
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.227
CYP3A4-substrate:	0.518

ADMET: Excretion

Clearance (CL):	9.313
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.424
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.105
Skin Sensitization:	0.933
Carcinogencity:	0.202
Eye Corrosion:	0.564
Eye Irritation:	0.86
Respiratory Toxicity:	0.773

Download Data

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

Natural Product: NPC186554

Natural Product ID:	NPC186554
*Common Name:**	10Alpha-Hydroxycadinan-4-Ene-3-One
IUPAC Name:	(4aR,5S,8R,8aR)-8-hydroxy-3,8-dimethyl-5-propan-2-yl-1,4a,5,6,7,8a-hexahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	XZKNRQNOZWYUMT-RMRHIDDWSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-9(2)11-5-6-15(4,17)13-8-14(16)10(3)7-12(11)13/h7,9,11-13,17H,5-6,8H2,1-4H3/t11-,12-,13+,15+/m0/s1
SMILES:	CC([C@@H]1CC[C@@]([C@H]2[C@H]1C=C(C)C(=O)C2)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509233
PubChem CID:	15275959
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
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	twig	n.a.	PMID[22474975]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31347365]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014350]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24241	Taiwania cryptomerioides	Species	Cupressaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	32.21	ug ml-1	PMID[523279]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	30.08	ug ml-1	PMID[523279]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	32.5	ug ml-1	PMID[523279]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	199.9	ug.mL-1	PMID[523279]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	=	50.0	ug.mL-1	PMID[523279]

☑ 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 NPC186554 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	168
0.1-0.2	1263
0.2-0.3	5632
0.3-0.4	14026
0.4-0.5	11001
0.5-0.6	6460
0.6-0.7	3415
0.7-0.8	663
0.8-0.85	46
0.85-0.9	11
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76966
0.9452	High Similarity	NPC207772
0.9315	High Similarity	NPC34110
0.9189	High Similarity	NPC253561
0.9189	High Similarity	NPC80088
0.9178	High Similarity	NPC151622
0.9178	High Similarity	NPC7629
0.9178	High Similarity	NPC472305
0.9054	High Similarity	NPC257666
0.9054	High Similarity	NPC266193
0.8947	High Similarity	NPC476809
0.8947	High Similarity	NPC469637
0.8933	High Similarity	NPC19443
0.8831	High Similarity	NPC473217
0.8831	High Similarity	NPC119229
0.8831	High Similarity	NPC226068
0.8734	High Similarity	NPC251170
0.8701	High Similarity	NPC472301
0.8608	High Similarity	NPC64600
0.8553	High Similarity	NPC197659
0.8537	High Similarity	NPC48107
0.8462	Intermediate Similarity	NPC172013
0.8442	Intermediate Similarity	NPC471409
0.8442	Intermediate Similarity	NPC275494
0.8375	Intermediate Similarity	NPC297398
0.8333	Intermediate Similarity	NPC263161
0.8333	Intermediate Similarity	NPC170394
0.8312	Intermediate Similarity	NPC97377
0.8293	Intermediate Similarity	NPC179591
0.8272	Intermediate Similarity	NPC470812
0.8267	Intermediate Similarity	NPC35656
0.8267	Intermediate Similarity	NPC247586
0.8228	Intermediate Similarity	NPC108955
0.8228	Intermediate Similarity	NPC138492
0.8228	Intermediate Similarity	NPC233352
0.8228	Intermediate Similarity	NPC824
0.8214	Intermediate Similarity	NPC119416
0.8205	Intermediate Similarity	NPC62336
0.8205	Intermediate Similarity	NPC74410
0.8205	Intermediate Similarity	NPC476808
0.8205	Intermediate Similarity	NPC189485
0.8193	Intermediate Similarity	NPC471792
0.8182	Intermediate Similarity	NPC470525
0.8182	Intermediate Similarity	NPC263582
0.8182	Intermediate Similarity	NPC180886
0.8182	Intermediate Similarity	NPC239758
0.8158	Intermediate Similarity	NPC22134
0.8143	Intermediate Similarity	NPC282694
0.8143	Intermediate Similarity	NPC194208
0.8143	Intermediate Similarity	NPC79576
0.8133	Intermediate Similarity	NPC84790
0.8125	Intermediate Similarity	NPC278459
0.8125	Intermediate Similarity	NPC55869
0.8118	Intermediate Similarity	NPC128672
0.8118	Intermediate Similarity	NPC134321
0.8108	Intermediate Similarity	NPC469914
0.8101	Intermediate Similarity	NPC308038
0.8095	Intermediate Similarity	NPC473229
0.8095	Intermediate Similarity	NPC472802
0.8077	Intermediate Similarity	NPC165711
0.8072	Intermediate Similarity	NPC472974
0.8052	Intermediate Similarity	NPC476795
0.8025	Intermediate Similarity	NPC93590
0.8025	Intermediate Similarity	NPC193347
0.8023	Intermediate Similarity	NPC116726
0.8	Intermediate Similarity	NPC2482
0.8	Intermediate Similarity	NPC472983
0.8	Intermediate Similarity	NPC163020
0.8	Intermediate Similarity	NPC472973
0.7975	Intermediate Similarity	NPC178852
0.7955	Intermediate Similarity	NPC476245
0.7952	Intermediate Similarity	NPC470574
0.7949	Intermediate Similarity	NPC250621
0.7945	Intermediate Similarity	NPC103734
0.7931	Intermediate Similarity	NPC134826
0.7922	Intermediate Similarity	NPC470299
0.7922	Intermediate Similarity	NPC38426
0.7907	Intermediate Similarity	NPC85173
0.7907	Intermediate Similarity	NPC191684
0.7901	Intermediate Similarity	NPC471898
0.7901	Intermediate Similarity	NPC473420
0.7901	Intermediate Similarity	NPC116797
0.7901	Intermediate Similarity	NPC477372
0.7901	Intermediate Similarity	NPC44963
0.7901	Intermediate Similarity	NPC121984
0.7901	Intermediate Similarity	NPC472684
0.7882	Intermediate Similarity	NPC471722
0.7882	Intermediate Similarity	NPC474677
0.7882	Intermediate Similarity	NPC328539
0.7882	Intermediate Similarity	NPC158778
0.7882	Intermediate Similarity	NPC471791
0.7882	Intermediate Similarity	NPC471793
0.7882	Intermediate Similarity	NPC206060
0.7875	Intermediate Similarity	NPC281138
0.7857	Intermediate Similarity	NPC94666
0.7857	Intermediate Similarity	NPC158393
0.7857	Intermediate Similarity	NPC72133
0.7857	Intermediate Similarity	NPC472304
0.7857	Intermediate Similarity	NPC74363
0.7857	Intermediate Similarity	NPC472986
0.7857	Intermediate Similarity	NPC475862
0.7857	Intermediate Similarity	NPC472985
0.7857	Intermediate Similarity	NPC276764
0.7857	Intermediate Similarity	NPC472488
0.7857	Intermediate Similarity	NPC472479
0.7841	Intermediate Similarity	NPC196227
0.7841	Intermediate Similarity	NPC103527
0.7831	Intermediate Similarity	NPC476412
0.7831	Intermediate Similarity	NPC144258
0.7821	Intermediate Similarity	NPC39362
0.7821	Intermediate Similarity	NPC114236
0.7816	Intermediate Similarity	NPC472975
0.7816	Intermediate Similarity	NPC472978
0.7816	Intermediate Similarity	NPC272746
0.7805	Intermediate Similarity	NPC302661
0.7805	Intermediate Similarity	NPC238991
0.7805	Intermediate Similarity	NPC470813
0.7805	Intermediate Similarity	NPC92226
0.7805	Intermediate Similarity	NPC48362
0.7805	Intermediate Similarity	NPC103486
0.7791	Intermediate Similarity	NPC86319
0.7791	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC275740
0.7791	Intermediate Similarity	NPC36668
0.7778	Intermediate Similarity	NPC157895
0.7778	Intermediate Similarity	NPC472478
0.7778	Intermediate Similarity	NPC104120
0.7778	Intermediate Similarity	NPC271104
0.7778	Intermediate Similarity	NPC148685
0.7765	Intermediate Similarity	NPC475740
0.7765	Intermediate Similarity	NPC73064
0.7765	Intermediate Similarity	NPC141292
0.7765	Intermediate Similarity	NPC30421
0.7753	Intermediate Similarity	NPC316215
0.7753	Intermediate Similarity	NPC271195
0.7753	Intermediate Similarity	NPC147232
0.775	Intermediate Similarity	NPC321514
0.775	Intermediate Similarity	NPC179028
0.7738	Intermediate Similarity	NPC474537
0.7738	Intermediate Similarity	NPC70685
0.7738	Intermediate Similarity	NPC8518
0.7738	Intermediate Similarity	NPC133954
0.7738	Intermediate Similarity	NPC263997
0.7738	Intermediate Similarity	NPC33663
0.7738	Intermediate Similarity	NPC132228
0.7738	Intermediate Similarity	NPC469993
0.7738	Intermediate Similarity	NPC6185
0.7738	Intermediate Similarity	NPC241512
0.7738	Intermediate Similarity	NPC29447
0.7722	Intermediate Similarity	NPC92080
0.7722	Intermediate Similarity	NPC78935
0.7711	Intermediate Similarity	NPC251475
0.7711	Intermediate Similarity	NPC49019
0.7711	Intermediate Similarity	NPC102197
0.7711	Intermediate Similarity	NPC169941
0.7711	Intermediate Similarity	NPC105173
0.7711	Intermediate Similarity	NPC105803
0.7711	Intermediate Similarity	NPC53733
0.7711	Intermediate Similarity	NPC66764
0.7711	Intermediate Similarity	NPC110150
0.7703	Intermediate Similarity	NPC197089
0.7701	Intermediate Similarity	NPC474209
0.7701	Intermediate Similarity	NPC126993
0.7701	Intermediate Similarity	NPC475823
0.7692	Intermediate Similarity	NPC162164
0.7683	Intermediate Similarity	NPC225515
0.7683	Intermediate Similarity	NPC189237
0.7683	Intermediate Similarity	NPC149237
0.7683	Intermediate Similarity	NPC475665
0.7683	Intermediate Similarity	NPC90055
0.7674	Intermediate Similarity	NPC471724
0.7674	Intermediate Similarity	NPC292491
0.7674	Intermediate Similarity	NPC143767
0.7674	Intermediate Similarity	NPC72397
0.7674	Intermediate Similarity	NPC131470
0.7674	Intermediate Similarity	NPC474925
0.7674	Intermediate Similarity	NPC310752
0.7667	Intermediate Similarity	NPC469545
0.7667	Intermediate Similarity	NPC61369
0.7667	Intermediate Similarity	NPC5532
0.7667	Intermediate Similarity	NPC117133
0.7662	Intermediate Similarity	NPC160817
0.7662	Intermediate Similarity	NPC144627
0.7654	Intermediate Similarity	NPC477371
0.7654	Intermediate Similarity	NPC215843
0.7654	Intermediate Similarity	NPC27817
0.7654	Intermediate Similarity	NPC472490
0.7654	Intermediate Similarity	NPC474113
0.7654	Intermediate Similarity	NPC231431
0.7647	Intermediate Similarity	NPC6979
0.7647	Intermediate Similarity	NPC474732
0.7647	Intermediate Similarity	NPC474733
0.7647	Intermediate Similarity	NPC31564
0.7647	Intermediate Similarity	NPC194417
0.7647	Intermediate Similarity	NPC474778
0.7647	Intermediate Similarity	NPC145879
0.7647	Intermediate Similarity	NPC203795
0.7647	Intermediate Similarity	NPC73038
0.7647	Intermediate Similarity	NPC476043
0.7647	Intermediate Similarity	NPC213412

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 NPC186554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1746
0.2-0.3	3967
0.3-0.4	2270
0.4-0.5	598
0.5-0.6	200
0.6-0.7	153
0.7-0.8	48
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
0.8293	Intermediate Similarity	NPD3618	Phase 1
0.8293	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4221	Approved
0.8025	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD4695	Discontinued
0.7857	Intermediate Similarity	NPD5690	Phase 2
0.7831	Intermediate Similarity	NPD4197	Approved
0.7816	Intermediate Similarity	NPD6079	Approved
0.7791	Intermediate Similarity	NPD5328	Approved
0.7765	Intermediate Similarity	NPD3573	Approved
0.7738	Intermediate Similarity	NPD5329	Approved
0.7727	Intermediate Similarity	NPD4202	Approved
0.7703	Intermediate Similarity	NPD7331	Phase 2
0.7647	Intermediate Similarity	NPD4693	Phase 3
0.7647	Intermediate Similarity	NPD4138	Approved
0.7647	Intermediate Similarity	NPD4694	Approved
0.7647	Intermediate Similarity	NPD4623	Approved
0.7647	Intermediate Similarity	NPD5205	Approved
0.7647	Intermediate Similarity	NPD4519	Discontinued
0.7647	Intermediate Similarity	NPD4689	Approved
0.7647	Intermediate Similarity	NPD4690	Approved
0.7647	Intermediate Similarity	NPD4688	Approved
0.7647	Intermediate Similarity	NPD5280	Approved
0.7619	Intermediate Similarity	NPD3133	Approved
0.7619	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD3665	Phase 1
0.7614	Intermediate Similarity	NPD7515	Phase 2
0.759	Intermediate Similarity	NPD3667	Approved
0.7568	Intermediate Similarity	NPD7341	Phase 2
0.7531	Intermediate Similarity	NPD3617	Approved
0.7473	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD5221	Approved
0.7473	Intermediate Similarity	NPD5222	Approved
0.7473	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7748	Approved
0.7439	Intermediate Similarity	NPD4195	Approved
0.7419	Intermediate Similarity	NPD4696	Approved
0.7419	Intermediate Similarity	NPD5285	Approved
0.7419	Intermediate Similarity	NPD5286	Approved
0.7416	Intermediate Similarity	NPD5284	Approved
0.7416	Intermediate Similarity	NPD5281	Approved
0.7412	Intermediate Similarity	NPD4786	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD7902	Approved
0.7391	Intermediate Similarity	NPD5173	Approved
0.7386	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD4629	Approved
0.7363	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD5223	Approved
0.7308	Intermediate Similarity	NPD4691	Approved
0.7263	Intermediate Similarity	NPD5226	Approved
0.7263	Intermediate Similarity	NPD5224	Approved
0.7263	Intermediate Similarity	NPD5225	Approved
0.7263	Intermediate Similarity	NPD5211	Phase 2
0.7263	Intermediate Similarity	NPD4633	Approved
0.7241	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD4700	Approved
0.7188	Intermediate Similarity	NPD5174	Approved
0.7188	Intermediate Similarity	NPD5175	Approved
0.7179	Intermediate Similarity	NPD4137	Phase 3
0.7126	Intermediate Similarity	NPD1694	Approved
0.7113	Intermediate Similarity	NPD5141	Approved
0.7111	Intermediate Similarity	NPD4096	Approved
0.7089	Intermediate Similarity	NPD4747	Approved
0.7065	Intermediate Similarity	NPD6001	Approved
0.7065	Intermediate Similarity	NPD7900	Approved
0.7065	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4692	Approved
0.7059	Intermediate Similarity	NPD4139	Approved
0.7037	Intermediate Similarity	NPD4058	Approved
0.7011	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5695	Phase 3
0.697	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD6399	Phase 3
0.6947	Remote Similarity	NPD5696	Approved
0.6932	Remote Similarity	NPD1696	Phase 3
0.6923	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD5091	Approved
0.69	Remote Similarity	NPD6011	Approved
0.69	Remote Similarity	NPD4729	Approved
0.69	Remote Similarity	NPD4730	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.69	Remote Similarity	NPD5128	Approved
0.6897	Remote Similarity	NPD4788	Approved
0.6889	Remote Similarity	NPD5208	Approved
0.6889	Remote Similarity	NPD4518	Approved
0.6869	Remote Similarity	NPD7128	Approved
0.6869	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD5739	Approved
0.6869	Remote Similarity	NPD6402	Approved
0.6869	Remote Similarity	NPD6675	Approved
0.6869	Remote Similarity	NPD4768	Approved
0.6863	Remote Similarity	NPD6649	Approved
0.6863	Remote Similarity	NPD6650	Approved
0.6854	Remote Similarity	NPD6409	Approved
0.6854	Remote Similarity	NPD7334	Approved
0.6854	Remote Similarity	NPD5330	Approved
0.6854	Remote Similarity	NPD7521	Approved
0.6854	Remote Similarity	NPD6684	Approved
0.6854	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD6084	Phase 2
0.6842	Remote Similarity	NPD6083	Phase 2
0.6842	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6014	Approved
0.6832	Remote Similarity	NPD6012	Approved
0.6832	Remote Similarity	NPD6013	Approved
0.6832	Remote Similarity	NPD6373	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.6829	Remote Similarity	NPD4687	Approved
0.6829	Remote Similarity	NPD5733	Approved
0.6813	Remote Similarity	NPD6673	Approved
0.6813	Remote Similarity	NPD6904	Approved
0.6813	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD5701	Approved
0.679	Remote Similarity	NPD5276	Approved
0.6765	Remote Similarity	NPD5250	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6765	Remote Similarity	NPD5169	Approved
0.6765	Remote Similarity	NPD5249	Phase 3
0.6765	Remote Similarity	NPD4634	Approved
0.6765	Remote Similarity	NPD5251	Approved
0.6765	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5135	Approved
0.6765	Remote Similarity	NPD5248	Approved
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD5247	Approved
0.6757	Remote Similarity	NPD287	Approved
0.6739	Remote Similarity	NPD5692	Phase 3
0.6737	Remote Similarity	NPD7614	Phase 1
0.6733	Remote Similarity	NPD7320	Approved
0.6733	Remote Similarity	NPD5168	Approved
0.6703	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6903	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD8130	Phase 1
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD5215	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD5217	Approved
0.6699	Remote Similarity	NPD5216	Approved
0.6699	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6628	Remote Similarity	NPD7645	Phase 2
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4243	Approved
0.6571	Remote Similarity	NPD4632	Approved
0.6556	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7525	Registered
0.6542	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6008	Approved
0.6509	Remote Similarity	NPD5167	Approved
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD4784	Approved
0.6429	Remote Similarity	NPD4785	Approved
0.6429	Remote Similarity	NPD5290	Discontinued
0.642	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5360	Phase 3
0.6389	Remote Similarity	NPD6009	Approved
0.6389	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD6404	Discontinued
0.6364	Remote Similarity	NPD7640	Approved
0.6353	Remote Similarity	NPD6942	Approved
0.6353	Remote Similarity	NPD7339	Approved
0.6353	Remote Similarity	NPD4190	Phase 3
0.6353	Remote Similarity	NPD5275	Approved
0.6333	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6313	Approved
0.633	Remote Similarity	NPD6314	Approved
0.633	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD8035	Phase 2
0.6316	Remote Similarity	NPD8034	Phase 2
0.6306	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6868	Approved
0.6292	Remote Similarity	NPD8028	Phase 2
0.6289	Remote Similarity	NPD5654	Approved
0.6282	Remote Similarity	NPD368	Approved
0.6277	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7100	Approved
0.6273	Remote Similarity	NPD7101	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data