NPASS Compound

Natural Product: NPC106112

Natural Product ID	NPC106112
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S,3R,4S,4As,6Ar,6Bs,8As,12As,14Ar,14Br)-2,3-Dihydroxy-4,6A,6B,11,11,14B-Hexamethyl-1,2,3,4A,5,6,7,8,9,10,12,12A,14,14A-Tetradecahydropicene-4,8A-Dicarboxylic Acid
IUPAC Name	(2S,3R,4S,4aS,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms	NSC-382025
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL432530
PubChem CID	462205
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 82 86 0 0 0 0 0 0 0 0999 V2000 5.9334 2.1633 0.9331 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1191 0.9096 1.0369 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0691 0.4445 2.4943 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6575 -0.1553 0.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 -0.3495 -1.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5098 -0.9136 -0.7743 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5589 -0.9548 -1.9189 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5626 0.1544 -1.9656 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7490 0.3390 -0.7127 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6232 1.8355 -0.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5372 -0.1882 0.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9035 -0.7371 1.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5549 -0.9040 1.6237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2767 -0.2761 0.5131 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7389 -0.7095 0.5305 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9118 -2.2129 0.4718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1803 -0.3233 1.9580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6453 -0.2781 2.1464 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4308 0.2463 0.9856 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5447 0.9907 -0.0117 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4809 1.2682 -1.2035 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 -0.0494 -0.5109 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8842 0.3075 -1.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4376 0.6169 -1.7227 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6295 -0.2943 -0.7910 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6244 -1.6298 -1.4638 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0351 2.2321 0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3063 2.6094 1.6569 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2346 3.0915 -0.2206 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9732 -0.8373 0.2962 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1371 -1.5116 2.5962 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0288 -0.1494 0.4299 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6604 1.1801 0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7813 -2.3429 -0.3706 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4823 -2.7247 0.7968 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3441 -3.2621 -1.2173 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3337 3.0731 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7234 2.1267 1.7373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4756 2.2434 -0.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1224 0.8077 2.9388 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0794 -0.6574 2.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8949 0.9209 3.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7211 0.1038 -0.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7120 -1.1548 0.6552 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4517 -1.1053 -1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8058 0.6164 -1.6644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1902 -0.8271 -2.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1198 -1.9744 -2.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 0.0254 -2.8860 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1757 1.0799 -2.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5434 2.2967 -0.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5992 2.3448 -1.5575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1808 2.1781 0.1035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5868 -1.1028 2.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7154 -1.9976 1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7932 -0.4696 2.6295 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3810 0.8210 0.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6098 -2.4746 -0.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4984 -2.6169 1.3538 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0073 -2.8017 0.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8056 -1.1525 2.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6194 0.5644 2.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8459 0.4321 3.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2704 0.9055 1.2740 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1736 2.2436 -1.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4756 0.4535 -1.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5193 1.4328 -0.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3146 -0.8595 -0.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1368 -0.3901 -2.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4046 1.2589 -2.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0265 0.4704 -2.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3148 1.6683 -1.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1160 -2.4346 -0.9424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7039 -1.8698 -1.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1914 -1.5939 -2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9482 3.9948 0.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9723 -0.8015 0.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8497 -1.8549 2.0038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4160 -0.7411 1.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8111 1.7738 -0.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2305 1.7123 1.4441 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1316 -4.2538 -1.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 20 27 1 0 27 28 2 0 27 29 1 0 19 30 1 0 18 31 1 0 11 32 1 0 32 33 1 0 6 34 1 1 34 35 2 0 34 36 1 0 33 2 1 0 32 6 1 0 25 9 1 0 25 14 1 0 22 15 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 5 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 14 57 1 1 16 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 1 19 64 1 1 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 6 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 29 76 1 0 30 77 1 0 31 78 1 0 32 79 1 1 33 80 1 0 33 81 1 0 36 82 1 0 M END

Standard InCHIKey	IDGXIXSKISLYAC-VERRDANPSA-N
Standard InCHI	InChI=1S/C30H46O6/c1-25(2)11-13-30(24(35)36)14-12-27(4)17(18(30)15-25)7-8-20-26(3)16-19(31)22(32)29(6,23(33)34)21(26)9-10-28(20,27)5/h7,18-22,31-32H,8-16H2,1-6H3,(H,33,34)(H,35,36)/t18-,19-,20+,21-,22-,26+,27+,28+,29-,30-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H]([C@@H]([C@](C)([C@H]5CC[C@@]34C)C(=O)O)O)O)[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.33	Volume:	529.486 ? Van der Waals volume.
Dense:	0.949	LogP:	2.718 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.653 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.183 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.383	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.943	Fsp³:	0.867
MCE-18:	111.286 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.761	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.138 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.339	Promiscuous compounds:	0.078

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.672	MDCK Permeability:	-5.198
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.047	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.675

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.994
Plasma Protein Binding (PPB):	87.516%	Volume Distribution (VD):	-0.495
Fu:	9.71% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.942	BCRP inhibitor:	0.0
BSEP inhibitor:	0.176

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.237	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.017 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.911

Half-life (T1/2):

1.708

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.732
AMES Toxicity:	0.149	Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.087	Skin Sensitization:	0.976
Carcinogencity:	0.751	Eye Corrosion:	0.058
Eye Irritation:	0.369	Respiratory Toxicity:	0.841
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.764
Hematotoxicity:	0.717	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	0.828	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.038	Hek293 Cytotoxicity:	0.016
BCF:	0.749 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.688 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.339 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.462 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14703354]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800643]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	Brazil	n.a.	PMID[18177008]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10677	Prunus prostrata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26218	Prosopis africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27030	Commiphora sphaerocarpa	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10677	Prunus prostrata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26218	Prosopis africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10350	Erythrina speciosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27030	Commiphora sphaerocarpa	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27103	Satureja vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25797	Piper divaricatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26151	Santolina pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26847	Lecidea quernea	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25832	Helichrysum drakensbergense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17806	Richteria pyrethroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	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	Organism Name	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
ID50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT609	Individual protein	Human immunodeficiency virus type 1 protease	Human immunodeficiency virus 1	ID50	=	35.0	uM	PMID[8642563]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC106112 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	25724
0.1-0.2	21102
0.2-0.3	2407
0.3-0.4	342
0.4-0.5	181
0.5-0.6	65
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261935
0.8387	Intermediate Similarity	NPC271614
0.7656	Intermediate Similarity	NPC282616
0.7538	Intermediate Similarity	NPC111214
0.7385	Intermediate Similarity	NPC84319
0.7385	Intermediate Similarity	NPC52021
0.7385	Intermediate Similarity	NPC599947
0.7313	Intermediate Similarity	NPC35239
0.7273	Intermediate Similarity	NPC231063
0.7273	Intermediate Similarity	NPC282395
0.7273	Intermediate Similarity	NPC481360
0.7273	Intermediate Similarity	NPC110308
0.6716	Remote Similarity	NPC480946
0.6716	Remote Similarity	NPC130577
0.6716	Remote Similarity	NPC142415
0.6716	Remote Similarity	NPC102683
0.6618	Remote Similarity	NPC270768
0.6618	Remote Similarity	NPC59263
0.6618	Remote Similarity	NPC307282
0.6618	Remote Similarity	NPC210106
0.6618	Remote Similarity	NPC275809
0.6522	Remote Similarity	NPC472149
0.6522	Remote Similarity	NPC609452
0.6429	Remote Similarity	NPC298554
0.6377	Remote Similarity	NPC37038
0.6364	Remote Similarity	NPC604575
0.6286	Remote Similarity	NPC158141
0.6176	Remote Similarity	NPC280654
0.6143	Remote Similarity	NPC64872
0.6143	Remote Similarity	NPC25906
0.6056	Remote Similarity	NPC130278
0.6056	Remote Similarity	NPC88116
0.6	Remote Similarity	NPC474806
0.6	Remote Similarity	NPC133579
0.5972	Remote Similarity	NPC291028
0.5915	Remote Similarity	NPC182797
0.5915	Remote Similarity	NPC121798
0.5915	Remote Similarity	NPC156981
0.5915	Remote Similarity	NPC32118
0.5915	Remote Similarity	NPC234346
0.5915	Remote Similarity	NPC52169
0.5915	Remote Similarity	NPC488562
0.589	Remote Similarity	NPC201657
0.5789	Remote Similarity	NPC474727
0.5753	Remote Similarity	NPC200752
0.5753	Remote Similarity	NPC145667
0.5753	Remote Similarity	NPC120840
0.5694	Remote Similarity	NPC306541
0.5676	Remote Similarity	NPC132824
0.5676	Remote Similarity	NPC474963
0.5641	Remote Similarity	NPC188833
0.5616	Remote Similarity	NPC481314
0.56	Remote Similarity	NPC481316
0.5556	Remote Similarity	NPC198664
0.5541	Remote Similarity	NPC87095
0.5526	Remote Similarity	NPC296164
0.5526	Remote Similarity	NPC174663
0.5488	Remote Similarity	NPC204407
0.5455	Remote Similarity	NPC96580
0.5443	Remote Similarity	NPC481362
0.5422	Remote Similarity	NPC283849
0.5422	Remote Similarity	NPC28198
0.5422	Remote Similarity	NPC476123
0.5422	Remote Similarity	NPC606107
0.5405	Remote Similarity	NPC173744
0.5405	Remote Similarity	NPC204961
0.5405	Remote Similarity	NPC73004
0.5405	Remote Similarity	NPC71074
0.5405	Remote Similarity	NPC37221
0.5405	Remote Similarity	NPC605937
0.5333	Remote Similarity	NPC259733
0.5333	Remote Similarity	NPC158371
0.5333	Remote Similarity	NPC207922
0.5333	Remote Similarity	NPC228784
0.5333	Remote Similarity	NPC324341
0.5333	Remote Similarity	NPC32407
0.5333	Remote Similarity	NPC263548
0.5333	Remote Similarity	NPC601810
0.5333	Remote Similarity	NPC606320
0.5325	Remote Similarity	NPC324063
0.5294	Remote Similarity	NPC286347
0.5263	Remote Similarity	NPC247139
0.5256	Remote Similarity	NPC481315
0.5233	Remote Similarity	NPC100383
0.5195	Remote Similarity	NPC471588
0.5195	Remote Similarity	NPC25299
0.5195	Remote Similarity	NPC481322
0.5195	Remote Similarity	NPC130520
0.5169	Remote Similarity	NPC171007
0.5169	Remote Similarity	NPC190849
0.5128	Remote Similarity	NPC20235
0.5128	Remote Similarity	NPC299996
0.5128	Remote Similarity	NPC222047
0.5114	Remote Similarity	NPC294112
0.5114	Remote Similarity	NPC284807
0.5056	Remote Similarity	NPC266365
0.5056	Remote Similarity	NPC191410
0.5055	Remote Similarity	NPC198621
0.5055	Remote Similarity	NPC216940

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC106112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6665
0.1-0.2	2445
0.2-0.3	36
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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